A U-Turn in the Asymmetric Appel Reaction: Stereospecific Reduction of Diastereomerically Enriched Alkoxyphosphonium Salts Allows the Asymmetric Synthesis of P-Stereogenic Phosphanes and Phosphane Boranes

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Title: A U-Turn in the Asymmetric Appel Reaction: Stereospecific Reduction of Diastereomerically Enriched Alkoxyphosphonium Salts Allows the Asymmetric Synthesis of P-Stereogenic Phosphanes and Phosphane Boranes
Authors: Rajendran, Kamalraj V.
Kudavalli, Jaya S.
Dunne, Katherine S.
Gilheany, Declan G.
Permanent link: http://hdl.handle.net/10197/4936
Date: 5-Apr-2012
Abstract: An efficient one-pot synthesis has been developed of enantioenriched P-stereogenic phosphanes and phosphane boranes from the corresponding racemic phosphanes in excellent yield under asymmetric Appel conditions. The chiral auxiliary (menthol) can also be recovered unchanged. The simple and efficient protocol significantly expands the scope of our asymmetric Appel process. The crucial step in the preparation involves stereospecific reduction of intermediate diastereomeric alkoxyphosphonium salts, which are obtained in the reaction of phosphane, hexachloroacetone, and menthol. Thereby, reaction with LiAlH4 or NaBH4 gives the corresponding phosphanes or phosphane boranes, respectively.
Type of material: Journal Article
Publisher: Wiley
Copyright (published version): 2012 WILEY-VCH Verlag GmbH & Co.
Keywords: Phosphanes;Boranes;Chirality;Asymmetric synthesis;Reduction
DOI: 10.1002/ejoc.201200285
Language: en
Status of Item: Peer reviewed
Appears in Collections:Chemistry Research Collection

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