Organocatalytic Michael Addition/Intramolecular Julia–Kocienski Olefination for the Preparation of Nitrocyclohexenes

An asymmetric organocatalytic [3 + 3] annulation strategy based on a Michael addition/intramolecular Julia–Kocienski olefination sequence has been developed for the synthesis of 4-substituted-5-nitrocyclohex-1-ene compounds. The strategy is an alternative to the direct reluctant enantioselective Die...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-11, Vol.78 (21), p.10737-10746
Main Authors: Rodrigo, Eduardo, García Ruano, José Luis, Cid, M. Belén
Format: Article
Language:English
Subjects:
Catalysis
Cyclohexenes - chemistry
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Nitro Compounds - chemistry
Stereoisomerism
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Summary:An asymmetric organocatalytic [3 + 3] annulation strategy based on a Michael addition/intramolecular Julia–Kocienski olefination sequence has been developed for the synthesis of 4-substituted-5-nitrocyclohex-1-ene compounds. The strategy is an alternative to the direct reluctant enantioselective Diels–Alder approach. The potential of the methodology has been demonstrated with a concise enantioselective formal synthesis of trandolapril.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo401686u