1,2‐Asymmetric Induction in the Ketene Claisen Rearrangement of Allyl Sulfides | Zendy

Nubbemeyer Udo | Zendy; Öhrlein Reinhold | Zendy; Gonda Jozef | Zendy; Ernst Beat | Zendy; Belluš Daniel | Zendy

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1,2‐Asymmetric Induction in the Ketene Claisen Rearrangement of Allyl Sulfides

Author(s) -

Nubbemeyer Udo,

Öhrlein Reinhold,

Gonda Jozef,

Ernst Beat,

Belluš Daniel

Publication year - 1991

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199114651

Subject(s) - ketene , optically active , claisen rearrangement , chemistry , asymmetric induction , carroll rearrangement , medicinal chemistry , stereochemistry , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis

Optically active α‐siloxycarbonates are converted to optically active allylsulfides 1 . These intermediates are allowed to react with dichloroketene (generated in situ) leading to optically active α,α‐dichloro‐β‐vinyl‐γ‐siloxy‐substituted thioesters 2 . The assumed transition state is represented by 3 . This ketene‐Claissen rearrangement shows complete 1,2‐asymmetric induction in all of the cases examined. Reductive dechlorination of the γ‐siloxy‐substituted thioesters provides optically active 3,4‐ cis ‐distubstituted γ‐lactones. R = Me, i Pr, C 2 H 4 OTBDMS; TBDMS = tert ‐butyldimethylsilyl.

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