Rajendran, Kamalraj V.Kamalraj V.RajendranKudavalli, Jaya S.Jaya S.KudavalliDunne, Katherine S.Katherine S.DunneGilheany, Declan G.Declan G.Gilheany2013-11-192013-11-192012 WILEY2012-04-05European Journal of Organic Chemistryhttp://hdl.handle.net/10197/4936An 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.enThis is the author's version of the following article: Rajendran, K. V., Kudavalli, J. S., Dunne, K. S. and Gilheany, D. G. (2012), 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. Eur. J. Org. Chem., 2012: 2720–2723 which has been published in final form at http://dx.doi.org/10.1002/10.1002/ejoc.201200285PhosphanesBoranesChiralityAsymmetric synthesisReductionJournal Article2012142720272310.1002/ejoc.2012002852013-10-10https://creativecommons.org/licenses/by-nc-nd/3.0/ie/