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1,2,3-Triazole Bound Au(I) (TA-Au) as Chemoselective Catalysts in Promoting Asymmetric Synthesis of Substituted Allenes

Dawei Wang, Lekh Nath S. Gautam, Cynthia Bollinger, Aleksandra Harris, Minyong Li and Xiaodong Shi*

*C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, United States, Email: xmshiusf.edu

D. Wang, L. N. S. Gautam, C. Bollinger, A. Harris, M. Li, X. Shi, Org. Lett., 2011, 13, 2618-2621.

DOI: 10.1021/ol200714h


Abstract

Triazole-Au (TA-Au) complexes are effective chemoselective catalysts in promoting propargyl ester/ether 3,3-rearrangements. Unlike other reported Au catalysts, TA-Au provided effective chirality transfer without racemization over a long period of time, giving enantioenriched allenes with excellent stereoselectivity in excellent yields.

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Key Words

Rearrangements


ID: J54-Y2011-1480