Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 14, Pages 2720-2723Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200285
Keywords
Phosphanes; Boranes; Chirality; Asymmetric synthesis; Reduction
Categories
Funding
- Science Foundation Ireland (SFI) [08/RFP/CHE1251, 09/IN.1/B2627]
- Science Foundation Ireland (SFI) [08/RFP/CHE1251] Funding Source: Science Foundation Ireland (SFI)
Ask authors/readers for more resources
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available