Highly stereoselective and easy synthesis of enantiopure phosphoranyl oxiranes

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

doi:10.1016/j.tetasy.2007.10.036

Highly stereoselective and easy synthesis of enantiopure phosphoranyl oxiranes

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

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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
Pages (from-to)	2617-2620
Journal	Tetrahedron Asymmetry
Volume	18
Issue number	22
DOIs	https://doi.org/10.1016/j.tetasy.2007.10.036
Publication status	Published - 12 Nov 2007

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10.1016/j.tetasy.2007.10.036

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title = "Highly stereoselective and easy synthesis of enantiopure phosphoranyl oxiranes",

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. {\textcopyright} 2007 Elsevier Ltd. All rights reserved.",

author = "Ona Illa and {\'A}ngel {\'A}lvarez-Larena and Antoine Baceiredo and Vicen{\c c} Branchadell and Ortu{\~n}o, {Rosa M.}",

year = "2007",

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doi = "10.1016/j.tetasy.2007.10.036",

language = "English",

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T1 - Highly stereoselective and easy synthesis of enantiopure phosphoranyl oxiranes

AU - Illa, Ona

AU - Álvarez-Larena, Ángel

AU - Baceiredo, Antoine

AU - Branchadell, Vicenç

AU - Ortuño, Rosa M.

PY - 2007/11/12

Y1 - 2007/11/12

N2 - 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.

AB - 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.

U2 - 10.1016/j.tetasy.2007.10.036

DO - 10.1016/j.tetasy.2007.10.036

M3 - Article

VL - 18

SP - 2617

EP - 2620

IS - 22

ER -

Highly stereoselective and easy synthesis of enantiopure phosphoranyl oxiranes

Abstract

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