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

著者情報

キーワード: chiral sulfoxide, chiral 1,3-oxazoline, chiral ligand, asymmetric Diels–Alder reaction, Lewis acid, copper catalyst

ジャーナルフリー

2002 年 50 巻 3 号 p. 372-379

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

詳細

抄録

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.

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