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Highly Enantioselective Conjugate Addition of Dialkylzinc Reagents to Acyclic Nitroalkenes: A Catalytic Route to 2-Amino Acids, Aldehydes, and Alcohols

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, Email: feringachem.rug.nl

A. Duursma, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc., 2003, 125, 3700-3701.

DOI: 10.1021/ja029817d


Abstract

Copper-catalyzed conjugate addition of dialkylzing reagents to acyclic nitroalkenes using a chiral phosphoramidite ligand gave products in enantioselectivities up to 98%. Routes to (functionalized) 2-amino aldehydes, acids, and alcohols are described.

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Key Words

Nitro compounds


ID: J48-Y2003-1400