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Highly Diastereoselective Catalytic Meerwein-Ponndorf-Verley Reductions

Jingjun Yin,* Mark A. Huffman, Karen M. Conrad and Joseph D. Armstrong, III

*Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, jingjun_yinmerck.com

J. Yin, M. A. Huffman, K. M. Conrad, J. D. Armstrong, J. Org. Chem., 2006, 71, 840-843.

DOI: 10.1021/jo052121t (free Supporting Information)


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Abstract

A highly anti selective Meerwein-Ponndorf-Verley (MPV) reduction of protected α-amino aromatic ketones using catalytic aluminum isopropoxide gave ephedrine analogues in high yields and enantiopurity. In contrast, high syn selectivity was obtained with α-alkoxy ketones via Felkin-Ahn control.

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Key Words

Meerwein-Ponndorf-Verley Reduction


ID: J42-Y2006-310