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A General, Highly Enantioselective Method for the Synthesis of D and L α-Amino Acids and Allylic Amines

Young K. Chen, Alice E. Lurain and Patrick J. Walsh*

*P. Roy and Diane T. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, Email: pwalshsas.upenn.edu

Y. K. Chen. A. E. Lurain, P. J. Walsh, J. Am. Chem. Soc., 2002, 124, 12225-12231.

DOI: 10.1021/ja027271p (free Supporting Information)


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Abstract

A highly enantioselective and catalytic vinylation of aldehydes leads to allylic alcohols that are then transformed to the allylic amines via Overman's [3,3]-sigmatropic rearrangement of imidates. Oxidative cleavage of the allylic amines furnishes amino acids in good yields and excellent ee's. The scope and utility of this method are demonstrated by the synthesis of challenging allylic amines and their subsequent transformation to valuable nonproteinogenic amino acids, including both D and L configured (1-adamantyl)glycine.

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Catalytic Asymmetric Generation of (Z)-Disubstituted Allylic Alcohols

L. Salvi, S.-J. Jeon, E. L. Fisher, P. J. Carroll, P. J. Walsh, J. Am. Chem. Soc., 2007, 129, 16119-16125.


Key Words

Allylic Alcohols, Allylic Amines, Overman Rearrangement, Oxidative Cleavage, Sodium Periodate, Ruthenium


ID: J48-Y2002-1300