Tetrahedron: Asymmetry

Asymmetric induction in the conjugate addition of thioacetic acid to methacrylamides with chiral auxiliaries

BH Kim, HB Lee, JK Hwang, YG Kim

Index: Kim, Byung Hyun; Lee, Hee Bong; Hwang, Jae Kwang; Kim, Young Gyu Tetrahedron Asymmetry, 2005 , vol. 16, # 6 p. 1215 - 1220

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Citation Number: 40

Abstract

The conjugate addition of thioacetic acid to methacrylamides with chiral C2-symmetric trans- 2, 5-disubstituted pyrrolidines afforded the addition products in excellent stereoselectivities (> 99% de) and good yields (80–90%). The high selectivity was attributed mainly to the steric effect of the chiral auxiliaries. The cyclic nature of the chiral auxiliaries seemed also important for both the stereoselectivity and the reaction rate. Acidic hydrolysis of the ...