期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2012, 期 14, 页码 2720-2723出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200285
关键词
Phosphanes; Boranes; Chirality; Asymmetric synthesis; Reduction
资金
- Science Foundation Ireland (SFI) [08/RFP/CHE1251, 09/IN.1/B2627]
- Science Foundation Ireland (SFI) [08/RFP/CHE1251] Funding Source: Science Foundation Ireland (SFI)
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.
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