Lewis Acid-Catalyzed Asymmetric Diels–Alder Reactions Using Chiral Sulfoxide Ligands: Chiral 2-(Arylsulfinylmethyl)-1,3-oxazoline Derivatives

Kazuhiro Watanabe; Takashi Hirasawa; Kunio Hiroi

doi:10.1248/cpb.50.372

Regular Articles

Lewis Acid-Catalyzed Asymmetric Diels–Alder Reactions Using Chiral Sulfoxide Ligands: Chiral 2-(Arylsulfinylmethyl)-1,3-oxazoline Derivatives

Kazuhiro Watanabe, Takashi Hirasawa, Kunio Hiroi

Author information

Keywords: chiral sulfoxide, chiral 1,3-oxazoline, chiral ligand, asymmetric Diels–Alder reaction, Lewis acid, copper catalyst

JOURNAL FREE ACCESS

2002 Volume 50 Issue 3 Pages 372-379

DOI https://doi.org/10.1248/cpb.50.372

Details

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.

Corresponding author

Register with J-STAGE for free!