Lewis acid-catalyzed asymmetric diels-alder reactions using chiral sulfoxide ligands: chiral 2-(arylsulfinylmethyl)-1, 3-oxazoline derivatives.

K Watanabe, T Hirasawa, K Hiroi

Index: Watanabe, Kazuhiro; Hirasawa, Takashi; Hiroi, Kunio Chemical and pharmaceutical bulletin, 2002 , vol. 50, # 3 p. 372 - 379

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Citation Number: 26

Abstract

New chiral sulfoxide-1, 3-oxazoline ligands have been developed as chiral ligands for Lewis acid-catalyzed asymmetric Diels–Alder reactions. The use of chiral sulfinyl 1, 3-oxazoline ligands in copper (II)-catalyzed asymmetric Diels–Alder reactions provided an endo cycloadduct as a major product with moderate enantioselectivity. A rationale is proposed for the mechanism of the asymmetric induction.