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

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

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139

J. Am. Chem. Soc., 2003, 125 (12), pp 3442–3443

DOI: 10.1021/ja034366y

Publication Date (Web): March 4, 2003

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, tfj@mit.edu

Abstract

A highly enantioselective method for catalytic reductive coupling of alkynes and aldehydes is described. Allylic alcohols are afforded with complete E/Z selectivity, generally >95:5 regioselectivity, and in up to 96% ee. In conjunction with ozonolysis, this process is complementary to existing methods of enantioselective α-hydroxy ketone synthesis.

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Published In Issue March 26, 2003
Received January 27, 2003

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Communication

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

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

A New Stereoselective Method for the Preparation of Allylic Alcohols

Alkene-Directed, Nickel-Catalyzed Alkyne Coupling Reactions

Ligand-Dependent Scope and Divergent Mechanistic Behavior in Nickel-Catalyzed Reductive Couplings of Aldehydes and Alkynes

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