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 Shū 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
J. Am. Chem. Soc., 2007, 129 (17), pp 5364–5365
DOI: 10.1021/ja0709730
Publication Date (Web): April 11, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, skobayas@mol.f.u-tokyo.ac.jp

Abstract

Abstract Image

A novel catalyst system based on complexes of calcium which promote the catalytic asymmetric 1,4-addition reactions and [3+2] cycloaddition reactions of α-amino acid derivatives with α,β-unsaturated carbonyl compounds have been developed. 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. A wide range of α,β-unsaturated esters and amides were applicable, and other glycine and even dl-alanine derivatives reacted with several α,β-unsaturated carbonyl compounds to afford the corresponding substituted pyrrolodine derivatives in high yields with excellent diastereo- and enantioselectivities. In the reactions with dl-alanine derivatives, quaternary asymmetric carbons were constructed efficiently.

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History

  • Published In Issue May 02, 2007
  • Received February 22, 2007

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