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Enantioselective Prévost and Woodward reactions using chiral hypervalent iodine(III): switchover of stereochemical course of an optically active 1,3-dioxolan-2-yl cation.

Authors
  • Fujita, Morifumi
  • Wakita, Mikimasa
  • Sugimura, Takashi
Type
Published Article
Journal
Chemical Communications
Publisher
The Royal Society of Chemistry
Publication Date
Apr 07, 2011
Volume
47
Issue
13
Pages
3983–3985
Identifiers
DOI: 10.1039/c1cc10129c
PMID: 21321775
Source
Medline
License
Unknown

Abstract

Optically active 1,3-dioxolan-2-yl cation intermediates were generated during enantioselective dioxyacetylation of alkene with chiral hypervalent iodine(III). Regioselective attack of a nucleophile toward the intermediate resulted in reversal of enantioselectivity of the dioxyacetylation.

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