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Synfacts 2007(6): 0608-0608  
DOI: 10.1055/s-2007-968494
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

ZACA-Lipase-Catalyzed Acetylation Synergy

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
Z. Huang, Z. Tan, T. Novak, G. Zhu, E. Negishi*
Purdue University, West Lafayette, USA
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Publikationsdatum:
22. Mai 2007 (online)

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Significance

Negishi has extended his Zr-catalyzed asymmetric carboalumination of alkenes (ZACA) strategy to a ZACA-lipase acetylation strategy. Under Zr catalysis, simple alkenes are carboaluminated with AlMe3 and subsequently acetylated to give enantioenriched 2-alkyl-1-alkanols as well as the corresponding enantioenriched 2-alkyl-1-O-acetylated compounds. After purification ee values of >98% are obtained in many cases. In situations where simple crystallization is difficult, the production of 98-99% ee by this method is a great alternative.