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Chiral Calcium Complexes as Brønsted Base Catalysts for Asymmetric Addition of α-Amino Acid Derivatives to α,β-Unsaturated Carbonyl Compounds

Susumu Saito, Tetsu Tsubogo and Shu Kobayashi*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science Technology Agency (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Email: skobayasmol.f.u-tokyo.ac.jp

S. Saito, T. Tsubogo, S. Kobayashi, J. Am. Chem. Soc., 2007, 129, 5364-5365.

DOI: 10.1021/ja0709730 (free Supporting Information)


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Abstract

Chiral complexes of calcium promote asymmetric 1,4-addition reactions and [3+2] cycloaddition reactions of α-amino acid derivatives with α,β-unsaturated carbonyl compounds. The reactions proceeded smoothly in the presence of 5-10 mol % of the chiral calcium catalyst to afford the desired adducts in high yields with high diastereo- and enantioselectivities.

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Key Words

α-Amino Acids, Conjugate Addition, Pyrrolidines


ID: J48-Y2007-1380