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Catalytic Asymmetric Reductive Coupling of Alkynes and Aldehydes: Enantioselective Synthesis of Allylic Alcohols and α-Hydroxy Ketones

Karen M. Miller, Wei-Sheng Huang and Timothy F. Jamison*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, Email: tfjmit.edu

K. M. Miller, W.-S. Huang, T. F. Jamison, J. Am. Chem. Soc., 2003, 125, 3442-3443.

DOI: 10.1021/ja034366y (free Supporting Information)


Abstract

A highly enantioselective method for catalytic reductive coupling of alkynes and aldehydes afforded allylic alcohols with complete E/Z selectivity, generally >95:5 regioselectivity, and in up to 96% ee. In conjunction with ozonolysis, this process allows the enantioselective synthesis of α-hydroxy ketones.

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Key Words

Allylic Alcohols, α-Hydroxy Ketones, Ozonolysis, Ozone


ID: J48-Y2003-1390