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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,

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

DOI: 10.1021/jo052121t

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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