Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 37, Pages 12841-12843Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja1054912
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- CNRS
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A very simple, one-step highly diastereoselective synthesis of bulky, configurationally and air-stable P-chiral tricyclic phosphines 3, showing an exceptionally strong nucleophilic character, has been developed. This method involves the reaction of the stable phosphonium sila-ylide 1 with aryl- and alkyl-substituted acetylene derivatives. Starting from commercially available chiral (R,S)-(+)-endo-2-norborneol, the corresponding enantiomerically pure phosphines were obtained with excellent enantioselectivities (ee >= 99%) and high chemical yields.
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