Catalytic asymmetric Diels–Alder reactions of α-thioacrylates for the preparation of norbornenone

Varinder K. Aggarwal; Emma S. Anderson; D. Elfyn Jones; Kerstin B. Obierey; Robert Giles

doi:10.1039/A805366I

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Chemical Communications

Issue 18, 1998

Urgent high quality communications from across the chemical sciences.

Impact Factor 6.169 100 Issues per Year Indexed in MEDLINE

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Catalytic asymmetric Diels–Alder reactions of α-thioacrylates for the preparation of norbornenone

Varinder K. Aggarwal, Emma S. Anderson, D. Elfyn Jones, Kerstin B. Obierey and Robert Giles

Chem. Commun., 1998, 1985-1986

DOI: 10.1039/A805366I

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Cu^II–bisoxazoline complexes catalyse the asymmetric Diels–Alder cycloaddition of α-thioacrylates with cyclopentadiene to give the cycloadducts in up to 92% yield, 88% de and >95% ee for the endo product; deprotection gives good yields of (1S,4S)-norbornenone with high enantioselectivity.

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Varinder K. Aggarwal
Emma S. Anderson
D. Elfyn Jones
Kerstin B. Obierey
Robert Giles

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Catalytic asymmetric Diels–Alder reactions of α-thioacrylates for the preparation of norbornenone

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