Bifunctional thiourea-catalyzed enantioselective double Michael reaction of γ,δ-unsaturated β-ketoester to nitroalkene: asymmetric synthesis of ()-epibatidine - ScienceDirect
摘要：
The asymmetric synthesis of 4-nitrocyclohexanone derivatives has been accomplished by enantioselective double Michael additions of γ,δ-unsaturated β-ketoesters to nitroalkenes using a catalytic amount of bifunctional thiourea and TMG. The three contiguous stereogenic centers of the obtained products were constructed with good to high diastereoselectivity and up to 92% ee. The biologically active natural product, ()-epibatidine, has been synthesized from the intermediate 11a in seven steps in 30% overall yield.
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关键词：
Thiourea Organocatalyst Michael reaction Asymmetric synthesis γ,δ-Unsaturated β-ketoester −)-Epibatidine
DOI：
10.1016/j.tetlet.2004.10.082
被引量：
年份：
2004
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