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

• Published in: Chemical & pharmaceutical bulletin Vol. 50; no. 3; pp. 372 - 379
• Main Authors: Watanabe, Kazuhiro, Hirasawa, Takashi, Hiroi, Kunio
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 01.03.2002; Pharmaceutical Soc Japan; Maruzen
• Subjects: Acids - chemistry; Alicyclic compounds; Alicyclic compounds, terpenoids, prostaglandins, steroids; asymmetric Diels–Alder reaction; Catalysis; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; chiral 1,3-oxazoline; chiral ligand; chiral sulfoxide; copper catalyst; Exact sciences and technology; Lewis acid; Life Sciences & Biomedicine; Organic chemistry; Oxazoles - chemistry; Pharmacology & Pharmacy; Physical Sciences; Preparations and properties; Science & Technology; Spectrum Analysis; Stereoisomerism; Sulfoxides - chemistry; Lewis acid; chiral ligand; MICHAEL; chiral 1,3-oxazoline; COMPLEXES; BIS(OXAZOLINE); NUCLEOPHILIC-SUBSTITUTION REACTIONS; asymmetric Diels-Alder reaction; ALLYLIC ALKYLATIONS; ENE REACTIONS; ORGANOSULFUR COMPOUNDS; COORDINATING ELEMENTS; FUNCTIONALITY; copper catalyst; BEARING; chiral sulfoxide; Endo stereoisomer; Magnesium Bromides; Diels Alder addition; Asymmetric induction; Asymmetric catalysis; Copper II Compounds; Stereoselectivity; Chiral auxiliary; Bicyclic compound; Conjugated dienic compound; Reaction mechanism; Sulfoxide; Ethyl ether; Chemical synthesis; Monocyclic compound; Oxygen nitrogen heterocycle
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.50.372

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.