Highly diastereoselective catalytic meerwein-ponndorf-verley reductions

J Yin, MA Huffman, KM Conrad…

Index: Yin, Jingjun; Huffman, Mark A.; Conrad, Karen M.; Armstrong III, Joseph D. Journal of Organic Chemistry, 2006 , vol. 71, # 2 p. 840 - 843

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Citation Number: 31

Abstract

Very practical synthesis of ephedrine analogues in high yields and enantiopurity was realized by a highly diastereoselective Meerwein-Ponndorf-Verley (MPV) reduction of protected α-amino aromatic ketones using catalytic aluminum isopropoxide. The high anti selectivity resulted from the chelation of the nitrogen anion to the aluminum. In contrast, high syn selectivity was obtained with α-alkoxy ketones and other compounds via Felkin-Ahn ...

~99%

~97%

~99%

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