Remote chiral induction in vinyl sulfonium salt-mediated ring expansion of hemiaminals into epoxide-fused azepines

Muhammad Yar; Matthew G. Unthank; Eoghan M. McGarrigle; Varinder K. Aggarwal

doi:10.1002/asia.201000817

Remote chiral induction in vinyl sulfonium salt-mediated ring expansion of hemiaminals into epoxide-fused azepines

Muhammad Yar, Matthew G. Unthank, Eoghan M. McGarrigle, Varinder K. Aggarwal

Research output: Contribution to journal › Article › peer-review

26 Citations (Scopus)

Abstract

The planet of the azepines: Epoxy-fused azepines have been synthesized in a highly selective reaction with hemiaminals and vinyl sulfonium salts. Stereochemistry is controlled by the substituent at the four- or five-position of the hemiaminal. The key step involves ring-opening of the hemiaminal, conjugate addition onto a vinyl sulfonium salt, and epoxidation of the aldehyde by the in situ formed sulfur ylide.

Original language	English
Pages (from-to)	372-375
Number of pages	4
Journal	Chemistry - An Asian Journal
Volume	6
Issue number	2
DOIs	https://doi.org/10.1002/asia.201000817
Publication status	Published - 1 Feb 2011
Externally published	Yes

Keywords

azepine
epoxidation
medium-ring compounds
nitrogen heterocycles
sulfur ylide

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10.1002/asia.201000817

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abstract = "The planet of the azepines: Epoxy-fused azepines have been synthesized in a highly selective reaction with hemiaminals and vinyl sulfonium salts. Stereochemistry is controlled by the substituent at the four- or five-position of the hemiaminal. The key step involves ring-opening of the hemiaminal, conjugate addition onto a vinyl sulfonium salt, and epoxidation of the aldehyde by the in situ formed sulfur ylide.",

keywords = "azepine, epoxidation, medium-ring compounds, nitrogen heterocycles, sulfur ylide",

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AU - Aggarwal, Varinder K.

PY - 2011/2/1

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AB - The planet of the azepines: Epoxy-fused azepines have been synthesized in a highly selective reaction with hemiaminals and vinyl sulfonium salts. Stereochemistry is controlled by the substituent at the four- or five-position of the hemiaminal. The key step involves ring-opening of the hemiaminal, conjugate addition onto a vinyl sulfonium salt, and epoxidation of the aldehyde by the in situ formed sulfur ylide.

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KW - epoxidation

KW - medium-ring compounds

KW - nitrogen heterocycles

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Remote chiral induction in vinyl sulfonium salt-mediated ring expansion of hemiaminals into epoxide-fused azepines

Abstract

Keywords

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