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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 23
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Original Articles

New Route for Synthesis of MeO-MOP

, &
Pages 3556-3560 | Received 02 Aug 2010, Published online: 04 Aug 2011
 

Abstract

The axially chiral monophosphine 2-(diphenylphosphino)-2′-methoxy-1,1′-binaphthyl (MeO-MOP) is a versatile ligand. We report a shorter (four steps from chiral BINOL), more atom-economical synthetic route to MeO-MOP. (R)-BINOL is transformed into its monomethyl ether by the Mitsunobu reaction, and the latter is reacted with triflic anhydride to give its triflate. The C-P coupling of the triflate and diphenylphosphine oxide catalyzed by palladium give a phosphine oxide, the precursor of (R)-MeO-MOP, which is reduced with trichlorosilane to furnish (R)-MeO-MOP.

ACKNOWLEDGMENTS

We thank the National Science Foundation of China (Grant No. 20672088), the Science and Technology Bureau of Sichuan (Grant No. 2011HH0016), and Cultivating Programme for Excellent Innovation Team of Chengdu University of Technology (No. HY0084) for financial support.

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