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Dual Stereoselectivity in the Dialkylzinc Reaction Using (-)-β-Pinene Derived Amino Alcohol Chiral Auxiliaries

Caitlin M. Binder, April Bautista, Marek Zaidlewicz, Marek P. Krzemiski, Allen Oliver and Bakthan Singaram*

*Department of Chemistry and Biochemistry, University of California, Santa Cruz, 1156 High Street, Santa Cruz, California 95064, Email: singaramchemistry.ucsc.edu

C. M. Binder, A. Bautista, M. Zaidlewicz, M. P. Krzemiski, A. Oliver, B. Singaram, J. Org. Chem., 2009, 74, 2337-2343.

DOI: 10.1021/jo802371z (free Supporting Information)


Abstract

Addition of diethylzinc to aromatic, aliphatic, and α,β-unsaturated aldehydes afforded secondary alcohols in high yield and enantiomeric excess in the presence of β-pinene derived amino alcohols 2-MAP and 3-MAP as chiral auxiliaries. These two amino alcohols provide antipodal enantiofacial selectivity in the dialkylzinc addition reaction.

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Key Words

1,2-addition


ID: J42-Y2009-0910