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Highly Enantioselective Conjugate Addition of Dialkylzinc Reagents to Acyclic Nitroalkenes: A Catalytic Route to β²-Amino Acids, Aldehydes, and Alcohols

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Ate Duursma, Adriaan J. Minnaard, and Ben L. Feringa*

Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands

J. Am. Chem. Soc., 2003, 125 (13), pp 3700–3701

DOI: 10.1021/ja029817d

Publication Date (Web): March 8, 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.

, feringa@chem.rug.nl

Abstract

Using chiral phosphoramidite ligand (S,R,R)-L1 in the conjugate addition to acyclic nitroalkenes for the first time, we obtained enantioselectivities up to 98%. The use of acyclic substrates with different dialkylzinc reagents provides a catalytic enantioselective route to (functionalized) β²-amino aldehydes, acids, and alcohols.

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Published In Issue April 02, 2003
Received December 19, 2002

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Communication

Highly Enantioselective Conjugate Addition of Dialkylzinc Reagents to Acyclic Nitroalkenes: A Catalytic Route to β²-Amino Acids, Aldehydes, and Alcohols