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_yin
merck.com
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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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
