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 language | English |
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Pages (from-to) | 2617-2620 |
Journal | Tetrahedron Asymmetry |
Volume | 18 |
Issue number | 22 |
DOIs | |
Publication status | Published - 12 Nov 2007 |