Asymmetric (4+3) cycloadditions of enantiomerically enriched epoxy enolsilanes

Brian Lo; Sarah Lam; Wing Tak Wong; Pauline Chiu

doi:10.1002/anie.201207427

Asymmetric (4+3) cycloadditions of enantiomerically enriched epoxy enolsilanes

Brian Lo, Sarah Lam, Wing Tak Wong, Pauline Chiu

Research output: Journal article publication › Journal article › Academic research › peer-review

59 Citations (Scopus)

Abstract

A f(oxy) allyl: The intermolecular (4+3) cycloaddition of enantiomerically enriched epoxy enolsilanes produces cycloadducts with up to 99 % ee, thus implying the reaction does not proceed by the putative achiral oxyallyl cation intermediate, but through a transiently chiral electrophile which retains the stereochemical information of the epoxide (see scheme; TES=triethylsilyl, Tf=trifluoromethanesulfonyl).

Original language	English
Pages (from-to)	12120-12123
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	48
DOIs	https://doi.org/10.1002/anie.201207427
Publication status	Published - 26 Nov 2012
Externally published	Yes

Keywords

allylic compounds
cycloaddition
heterocycles
stereoselectivity
synthetic methods

ASJC Scopus subject areas

Catalysis
General Chemistry

More information

10.1002/anie.201207427

Cite this

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title = "Asymmetric (4+3) cycloadditions of enantiomerically enriched epoxy enolsilanes",

abstract = "A f(oxy) allyl: The intermolecular (4+3) cycloaddition of enantiomerically enriched epoxy enolsilanes produces cycloadducts with up to 99 \% ee, thus implying the reaction does not proceed by the putative achiral oxyallyl cation intermediate, but through a transiently chiral electrophile which retains the stereochemical information of the epoxide (see scheme; TES=triethylsilyl, Tf=trifluoromethanesulfonyl).",

keywords = "allylic compounds, cycloaddition, heterocycles, stereoselectivity, synthetic methods",

author = "Brian Lo and Sarah Lam and Wong, \{Wing Tak\} and Pauline Chiu",

year = "2012",

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doi = "10.1002/anie.201207427",

language = "English",

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journal = "Angewandte Chemie - International Edition",

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AU - Lo, Brian

AU - Lam, Sarah

AU - Wong, Wing Tak

AU - Chiu, Pauline

PY - 2012/11/26

Y1 - 2012/11/26

N2 - A f(oxy) allyl: The intermolecular (4+3) cycloaddition of enantiomerically enriched epoxy enolsilanes produces cycloadducts with up to 99 % ee, thus implying the reaction does not proceed by the putative achiral oxyallyl cation intermediate, but through a transiently chiral electrophile which retains the stereochemical information of the epoxide (see scheme; TES=triethylsilyl, Tf=trifluoromethanesulfonyl).

AB - A f(oxy) allyl: The intermolecular (4+3) cycloaddition of enantiomerically enriched epoxy enolsilanes produces cycloadducts with up to 99 % ee, thus implying the reaction does not proceed by the putative achiral oxyallyl cation intermediate, but through a transiently chiral electrophile which retains the stereochemical information of the epoxide (see scheme; TES=triethylsilyl, Tf=trifluoromethanesulfonyl).

KW - allylic compounds

KW - cycloaddition

KW - heterocycles

KW - stereoselectivity

KW - synthetic methods

UR - https://www.scopus.com/pages/publications/84869989403

U2 - 10.1002/anie.201207427

DO - 10.1002/anie.201207427

M3 - Journal article

SN - 1433-7851

VL - 51

SP - 12120

EP - 12123

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 48

ER -

Asymmetric (4+3) cycloadditions of enantiomerically enriched epoxy enolsilanes

Abstract

Keywords

ASJC Scopus subject areas

More information

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