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ChemInform Abstract: Catalytic Asymmetric Diels—Alder Reactions of α-Thioacrylates for the Preparation of Norbornenone.

✍ Scribed by V. K. AGGARWAL; E. S. ANDERSON; D. E. JONES; K. B. OBIEREY; R. GILES

Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Catalytic Asymmetric Diels-Alder Reactions of α-Thioacrylates for the Preparation of Norbornenone.

-Cu(II)-catalyzed asymmetric Diels-Alder cycloaddition of α-thioacrylates (I) with excess cyclopentadiene using a bisoxazoline as chiral auxiliary provides the corresponding cycloadducts (III) in high yield and good to excellent stereoselectivity under optimized conditions. Deprotection of the adducts (III) affords enantio-enriched (1S,4S)norbornene (IV). -(AGGARWAL, V. K.;

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