期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2008, 期 8, 页码 1449-1457出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200701122
关键词
asymmetric synthesis; organocatalysis; Michael additions; Domino reactions; tandem reactions
Organocatalytic conjugate addition of 7-oxohept-2-enoate to nitrostyrene provided an omega-nitro-alpha,beta-unsaturated ester. Subsequent intramolecular cyclization afforded the highly functionalized cyclohexane carboester with four stereogenic centers with high diastereoselectivity and high enantioselectivity (> 99% ee). Some adducts were transformed into the intermediates of the synthesis of (-)-alpha- and (-)-beta-lycorane. Application of the reactions to the corresponding dialdehyde provided bicyclo [2.2.2]octanes. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
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