Highly stereoselective and easy synthesis of enantiopure phosphoranyl oxiranes

Ona Illa, Ángel Álvarez-Larena, Antoine Baceiredo, Vicenç Branchadell, Rosa M. Ortuño

Research output: Contribution to journalArticleResearchpeer-review

9 Citations (Scopus)

Abstract

The highly stereoselective synthesis of enantiopure phosphoranyl alkyl oxiranes has been accomplished by the addition of a nucleophilic stable phosphino(silyl)carbene to chiral aldehydes prepared from (-)-verbenone and d-mannitol, respectively. In the process, two new stereogenic centers are created one of them being on an oxirane quaternary carbon. The excellent π-facial diastereoselection of the aldehydes combined with the diastereoselectivity of the carbene addition allowed us to synthesize the title compounds as single stereoisomers with well defined absolute configuration. © 2007 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)2617-2620
JournalTetrahedron Asymmetry
Volume18
Issue number22
DOIs
Publication statusPublished - 12 Nov 2007

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