ライフサイエンスコーパス: sigmatropic rearrangement

1 lowed by a probable 1,3-OAc migration ([3,3]-sigmatropic rearrangement).

2 oxonium ylide formation followed by a [2,3]-sigmatropic rearrangement.

3 described as a concerted asynchronous [3,3]-sigmatropic rearrangement.

4 alpha-chloro sulfide intermediates and [2,3] sigmatropic rearrangement.

5 rmediate and facilitates the rate of the 3,3-sigmatropic rearrangement.

6 4 + 2) cyclohexenyl products through a [3,3]-sigmatropic rearrangement.

7 dolines via a thionium ylide-initiated [3,3]-sigmatropic rearrangement.

8 through the use of an Ireland-Claisen [3,3]-sigmatropic rearrangement.

9 e expected indane by an unusually facile 1,3-sigmatropic rearrangement.

10 commodity materials via the Ireland-Claisen sigmatropic rearrangement.

11 aza-arene N-oxides, triggering a rapid [3,3]-sigmatropic rearrangement.

12 athway alongside the thermally allowed [2,3]-sigmatropic rearrangement.

13 ycloaddition and N-alkenylisoxazoline [3,3']-sigmatropic rearrangement.

14 C-N bond formation, deprotonation, and a 3,3-sigmatropic rearrangement.

15 mixed acetal formation and subsequent [3,3] sigmatropic rearrangement.

16 a mixture of regioisomers upon heating via a sigmatropic rearrangement.

17 nverted to 3-hydroxy tetrahydropyridines via sigmatropic rearrangement.

18 luorescent indicator based on the 2-aza-Cope sigmatropic rearrangement.

19 pansion of the anionic intermediate by [1,3] sigmatropic rearrangement.

20 ate of hydrogenation relative to the rate of sigmatropic rearrangement.

21 titution via suprafacial allylic azide [3,3]-sigmatropic rearrangement.

22 d promotes its evolution to HCTD via a [1,2]-sigmatropic rearrangement.

23 e species becomes competitive with the [3,3]-sigmatropic rearrangement.

24 ilable tartrate derivative were obtained via sigmatropic rearrangement.

25 s formed immediately after the initial [3,3] sigmatropic rearrangement.

26 of oxonium ylide formation followed by [2,3]-sigmatropic rearrangement.

27 ations is combined with a diastereoselective sigmatropic rearrangement.

28 les are favored over the more familiar [3,3]-sigmatropic rearrangements.

29 ry expected for classically pericyclic [3,3] sigmatropic rearrangements.

30 (+)-latifoline (1) employing a tandem [3,3] sigmatropic rearrangement/[1,2] allyl shift as a key ste

31 gold catalyzed enantioselective tandem [3,3]-sigmatropic rearrangement-[2+2]-cyclization.

32 The reaction proceeds via [3,3]-sigmatropic rearrangement/5-exo-dig cyclization of N-pro

33 intramolecular transesterification and [1,5] sigmatropic rearrangement affords a series of helical co

34 gement (pseudopericyclic), and similar [3,3] sigmatropic rearrangements (all pericyclic), and detaile

35 featuring a Rh-mediated O-H insertion/[3,3]-sigmatropic rearrangement and subsequent alpha-ketol rea

36 nder the latter conditions resulted in [1,3]-sigmatropic rearrangement and subsequent oligomerization

37 Classic ACT transformations, including [3,3]-sigmatropic rearrangement and transition metal-catalyzed

38 om an unexpected and remarkably facile [1,3]-sigmatropic rearrangement, and a tactic to disfavor the

39 via a gold-catalyzed tautomerization, [3,3]-sigmatropic rearrangement, and cyclodehydration process.

40 ocyclization of the hexatriene system, [1,9]-sigmatropic rearrangement, and heterocyclic ring opening

41 functional theory (DFT) calculations of the sigmatropic rearrangement are in agreement with reactivi

42 Sigmatropic rearrangements are an important fundamental

43 s an additive increase the rate of the [3,3] sigmatropic rearrangement as well as the diastereoselect

44 as the tandem cyclization followed by [2,3]-sigmatropic rearrangement, as well as cyclization of the

45 cyclopropenation, sulfur ylide formation/2,3-sigmatropic rearrangement, as well as nitrogen ylide for

46 0(2,8)]tridec-10-ene (13TCT) undergoes [1,3] sigmatropic rearrangements at 315 degrees C in the gas p

47 The tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor rhodium

48 Subsequent in situ enantioselective [2,3]-sigmatropic rearrangement catalyzed by the isothiourea b

49 rough an interrupted Pummerer reaction/[3,3]-sigmatropic rearrangement/cyclization sequence to delive

50 lines efficiently from silver-mediated [3,3]-sigmatropic rearrangement/Diels-Alder reaction of 1,9-di

51 arrangements, as well as some typical [2, 3]-sigmatropic rearrangements, e.g., thermal rearrangements

52 diastereospecificity originates from a [3,3]-sigmatropic rearrangement followed by a sodium-assisted

53 nsient allenes by means of a strategic [2,3]-sigmatropic rearrangement followed by trapping of the re

54 of a stereoselective one-pot oxidative [3,3] sigmatropic rearrangement/Friedel-Crafts arylation that

55 e strategy is based on a [3,3]-allyl cyanate sigmatropic rearrangement from enantioenriched gamma-hyd

56 tero-Diels-Alder cycloadditions as well as a sigmatropic rearrangement have been located, and they al

57 [3,3]-Sigmatropic rearrangements have been widely utilized for

58 hat rapidly undergoes either [3,3]- or [5,5]-sigmatropic rearrangement in one-pot to form a 2-amino-2

59 tion pathway provides rare examples of [2,3]-sigmatropic rearrangement in this class of compounds as

60 rong experimental evidence that direct [3,5]-sigmatropic rearrangements in these molecules are favore

61 It is based on two subsequent [3,3]-sigmatropic rearrangements, in particular, Johnson-Clais

62 cluding [2 + 2] photocycloaddition and [3,3] sigmatropic rearrangement, indicating the possibility fo

63 isomerization process that occurs via [3,3]-sigmatropic rearrangement induced by high oxidation stat

64 roduct is formed via an intramolecular [3,3]-sigmatropic rearrangement instead of the previously prop

65 ion forms by a hemiketal-oxy-Cope type [3,3]-sigmatropic rearrangement-intramolecular aldol condensat

66 KOtBu-induced E2 elimination, undergo [3,3]-sigmatropic rearrangement/intramolecular 5-exo-dig cycli

67 Results of calculations on the [3,3] sigmatropic rearrangements involving additional transiti

68 ies on CaADH, while the exceptionally facile sigmatropic rearrangement is expected to drive computati

69 consistent with the observation that the 2,3-sigmatropic rearrangement is favored with donor/acceptor

70 A subsequent [3,3]-sigmatropic rearrangement is followed by intramolecular

71 ketyl radical-anion mechanism for the [3,3]-sigmatropic rearrangement is presented.

72 ions precedes a stereochemistry-determining sigmatropic rearrangement is reported.

73 hat the lowest energy pathway for each [3,5]-sigmatropic rearrangement is via an allowed, concerted p

74 N-Allyl enamines can undergo a [3,3] sigmatropic rearrangement known as a 3-aza-Cope (or amin

75 cond domino process, a [H]-shift and a [3,3]-sigmatropic rearrangement lead to the aromatization of t

76 e failed, we uncovered another set of tandem sigmatropic rearrangements, leading to vinyl imidate for

77 zomethine ylides, [3 + 2]-cycloaddition, 1,3-sigmatropic rearrangement, Michael addition, and Pictet-

78 tractive and highly diastereoselective [2,3]-sigmatropic rearrangement occurs when N-methyl-1,2,3,6-t

79 talin 55 is the oxyanionic-accelerated [3,3]-sigmatropic rearrangement of 37e.

80 heir alpha-position by an asynchronous [3,3]-sigmatropic rearrangement of a mixed acetal species whic

81 ds (78-89%) in a process involving the [1,4]-sigmatropic rearrangement of a nitrile-stabilized ammoni

82 dihydroxylation, and a stereoselective [2,3]-sigmatropic rearrangement of a selenoxide to effect a 1,

83 The base-induced [2,3]-sigmatropic rearrangement of a series of enantiopure 2-s

84 wn to be an effective catalyst for the [3,3]-sigmatropic rearrangement of a variety of substituted al

85 NEPHOS(AuCl)(2)), has been developed for the sigmatropic rearrangement of alkenyl-methylenecyclopropa

86 ve mechanisms of the gold(I)-catalyzed [3,3] sigmatropic rearrangement of allenyl vinyl ethers by den

87 development of an efficient oxidative [2,3]-sigmatropic rearrangement of allylic hydrazides, via sin

88 The [2,3]-sigmatropic rearrangement of allylic sulfoxides to allyl

89 Under certain conditions, the [2,3]-sigmatropic rearrangement of allyloxy carbonyl compounds

90 se of phase-transfer catalysis for the [2,3]-sigmatropic rearrangement of allyloxy carbonyl compounds

91 (II)-catalyzed oxonium ylide formation-[2,3] sigmatropic rearrangement of alpha-diazo-beta-ketoesters

92 abicyclo[5.3.0]decane ring system by a [3,3] sigmatropic rearrangement of an acylimmonium ion followe

93 rbocyclic core of these targets were a [2,3]-sigmatropic rearrangement of an allylic sulfur ylide to

94 conocene-promoted ring contraction and [3,3] sigmatropic rearrangement of an enynol.

95 eveloped via a dichlorocarbene insertion and sigmatropic rearrangement of an in situ generated ylide.

96 We find the barrier for sigmatropic rearrangement of chemisorbed hydrogen atoms

97 ence for a mechanism that involves the [3,3] sigmatropic rearrangement of divinylcyclopropanes.

98 he scope of the NCS-mediated amination/[2,3]-sigmatropic rearrangement of enantioenriched allylic sel

99 ed to the allylic amines via Overman's [3,3]-sigmatropic rearrangement of imidates.

100 systems are prepared by acid-catalyzed [3,3]-sigmatropic rearrangement of O-aryloximes.

101 nsformed directly to allenes through a [2,3]-sigmatropic rearrangement of propargyl phosphites.

102 mparative study of the Au(I)-catalyzed [3,3]-sigmatropic rearrangement of propargylic esters and prop

103 Sigmatropic rearrangement of spirocyclic pyrazoles to fu

104 Herein, we describe a gold-catalyzed sigmatropic rearrangement of sulfonium and selenium ylid

105 cationic gold(I)-catalyzed asymmetric [3,3]-sigmatropic rearrangement of sulfonium leads after cycli

106 er-catalyzed generation and subsequent [2,3]-sigmatropic rearrangement of sulfur ylides is strongly d

107 resolution is enabled by a spontaneous [3,3]-sigmatropic rearrangement of the allylic azide.

108 Products are obtained by [3,3]-sigmatropic rearrangement of the azasulfonium enolate or

109 The process involves a [3,3] sigmatropic rearrangement of the in situ generated mixed

110 Instead, a [3,3]-sigmatropic rearrangement of the initial cyclization int

111 ith the N-Boc-oxaziridine 1 results in [2,3]-sigmatropic rearrangement of the intermediate allylic N-

112 Quantum chemical calculations of a [3,3]sigmatropic rearrangement of the N,O-divinyl hydroxylami

113 rs at the terminal oxygen, followed by [2,3]-sigmatropic rearrangement of the pendant allyl group, in

114 The mechanism involves a [2,3]-sigmatropic rearrangement of the respective selenoxides

115 bsolute stereochemistry and (ii) a new [3,3]-sigmatropic rearrangement of the thiono-Claisen variety

116 promote thermodynamically unfavorable [3,3] sigmatropic rearrangements of 3,3-dicyano-1,5-dienes to

117 Earlier studies have shown that [3,3]-sigmatropic rearrangements of allyl esters are useful fo

118 The [2,3]- and [1,2]-sigmatropic rearrangements of ammonium ylides are studie

119 [2,3]-Sigmatropic rearrangements of beta-unsaturated sulfinyl

120 l computational study of the concerted [3,3] sigmatropic rearrangements of cis-1-iminyl-2-ketenylcycl

121 ta- and delta-eliminations, as well as [3,3]-sigmatropic rearrangements of esters are primarily pseud

122 rroles has been achieved via [3,3] and [1,3] sigmatropic rearrangements of O-vinyl oximes, respective

123 relative rate constants for ring opening and sigmatropic rearrangements of the dihydrophenanthrene in

124 rhodium-bound oxonium ylide formation, [2,3]-sigmatropic rearrangement, oxy-Cope rearrangement, enol-

125 The title [3,3] sigmatropic rearrangement proceeds in generally excellen

126 The 2,3-sigmatropic rearrangement proceeds through initial cleav

127 reochemically unscathed by competitive [3,3]-sigmatropic rearrangement processes.

128 C gives a modest yield of the initial [3,5]-sigmatropic rearrangement product, 2,6-diacetoxy-6-methy

129 refore affords the radical anion without any sigmatropic rearrangement products.

130 he semiquinone which is rapidly converted to sigmatropic rearrangement products.

131 essentially pericyclic), the 11 --> 12 [3,3] sigmatropic rearrangement (pseudopericyclic), and simila

132 The first example of a biocatalytic [2,3]-sigmatropic rearrangement reaction involving allylic sul

133 s-alkenes is evidenced by their formal [1,3]-sigmatropic rearrangement reactions and the rapid additi

134 Furthermore, we report on the limitations of sigmatropic rearrangement reactions of aryl allyl anilin

135 s via stereocontrolled cyanate-to-isocyanate sigmatropic rearrangement reactions of the corresponding

136 rgo thermal and photolytic cycloaddition/1,5-sigmatropic rearrangement reactions with 11a-d with N(2)

137 nic probe that selectively undergoes a [2,3]-sigmatropic rearrangement (seleno-Mislow-Evans rearrange

138 engineered to initiate a sulfimidation/[2,3]-sigmatropic rearrangement sequence in whole E. coli cell

139 rignard ring opening/allylic sulfoxide [2,3]-sigmatropic rearrangement sequence previously developed

140 anistic insight hinges on a reversible [3,3]-sigmatropic rearrangement step, supported by (1)H NMR st

141 f kinetic resolution, and the stereospecific sigmatropic rearrangement step, which proceeds with full

142 of dynamic trajectories in [1,2]- and [2,3]-sigmatropic rearrangements suggests a counterintuitive a

143 ey step in the synthesis, a sequential [2,3]-sigmatropic rearrangement/syn-elimination of an allyl su

144 A dearomative [3,3']-sigmatropic rearrangement that converts N-alkenylbenziso

145 on to N-fused pyrroles proceeded via a [3,3]-sigmatropic rearrangement, the analogous cycloisomerizat

146 cyclo[4.2.0]oct-2-ene (1a) undergoes a [1,3] sigmatropic rearrangement to 5-exo- and 5-endo-methoxybi

147 cyclo[4.2.0]oct-2-ene (1a) undergoes a [1,3] sigmatropic rearrangement to 5-methylbicyclo[2.2.2]oct-2

148 binaphthyl hydrazines undergo a facile [3,3]-sigmatropic rearrangement to afford enantiomerically enr

149 lowed by an orthoester Johnson-Claisen [3,3]-sigmatropic rearrangement to construct a sterically dema

150 active intermediate undergoes a pseudo-[1,4]-sigmatropic rearrangement to directly furnish heterocycl

151 The route relies on the aza-[2,3]-Wittig sigmatropic rearrangement to efficiently install the rel

152 ee major thermal rearrangements, namely, 3,3-sigmatropic rearrangement to form 1,2,3-triazine (2), al

153 incipally via SO2-N bond homolysis and [1,5] sigmatropic rearrangement to generate 37, 10 proceeded v

154 ive trans-1,3-pentadiene, 40 +/- 3% of [3,3]-sigmatropic rearrangement to give cis-3-penten-2-yl acet

155 give cis-1,3-pentadiene, 32 +/- 2% of [3,3]-sigmatropic rearrangement to give trans-3-penten-2-yl ac

156 lled stereoselective Mislow-Evans-type [2,3]-sigmatropic rearrangement to install the C5 stereocenter

157 ting ISDA cycloadduct either undergoes [3,3]-sigmatropic rearrangement to the more stable major IHDA

158 cycloaddition participate in a thermal [3,3] sigmatropic rearrangement to yield bicyclo[3.3.2]decadie

159 ns, ranging from cycloaddition reactions and sigmatropic rearrangements to C-H functionalizations, th

160 The most favored [3,3]-sigmatropic rearrangement transition state is bimodal, l

161 Several [3,3] sigmatropic rearrangement transition states were also lo

162 ged 16-acetate (2), which can form from 1 by sigmatropic rearrangement under basic conditions, batrac

163 sors are readily prepared and undergo smooth sigmatropic rearrangement upon exposure to iodosobenzene

164 The carbene undergoes two [1,2]-sigmatropic rearrangements via competing 1,2-C atom shif

165 Here, using a series of sequential [3,3]-sigmatropic rearrangements, we report the total synthesi

166 Three sigmatropic rearrangements were employed in building the

167 esting and unexpected [1,2]-Wittig and [1,3]-sigmatropic rearrangements were identified during the op

168 The disfavored [3,3]-sigmatropic rearrangement, which would produce the unobs

169 rmed through the use of a Still-Wittig [2,3]-sigmatropic rearrangement, while the trans mimic, the (E

170 Sigmatropic rearrangements, while rare in biology, offer

171 n demonstrated by combining the Mislow [2,3]-sigmatropic rearrangement with catalytic asymmetric hydr

172 These systems undergo the [3,3] sigmatropic rearrangement with high selectivity, with a

173 [2,3]-Sigmatropic rearrangements (Wittig rearrangements) of al

174 no-Claisen variety that is among the fastest sigmatropic rearrangements yet reported.