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

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 m...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 2002, Vol.50(3), pp.372-379
Hauptverfasser:	Watanabe, Kazuhiro, Hirasawa, Takashi, Hiroi, Kunio
Format:	Artikel
Sprache:	eng
Schlagworte:	Acids - chemistry Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids asymmetric Diels–Alder reaction Catalysis Chemistry chiral 1,3-oxazoline chiral ligand chiral sulfoxide copper catalyst Exact sciences and technology Lewis acid Organic chemistry Oxazoles - chemistry Preparations and properties Spectrum Analysis Stereoisomerism Sulfoxides - chemistry
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Zusammenfassung:	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.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.50.372