One-Pot Organocatalytic Enantioselective Michael-Michael-Aldol-Henry Reaction Cascade. A Facile Entry to the Steroid System with Six Contiguous Stereogenic Centers
One-Pot Organocatalytic Enantioselective Michael-Michael-Aldol-Henry Reaction Cascade. A Facile Entry to the Steroid System with Six Contiguous Stereogenic Centers
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DOI：
10.1021/ol501011t
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发表时间：
2014-05-16
期刊：
影响因子：
5.2
通讯作者：
Lee, Gene-Hsiang
中科院分区：
文献类型：
--
作者：
Jhuo, Dai-Huei;Hong, Bor-Cherng;Lee, Gene-Hsiang
开发了一种快速的方法，用于合成含有六个连续立体中心的高度功能化的类固醇系统，具有高的对映选择性(99%ee)。一锅法包括7-硝基-3-烯-2-酮和5-(1-甲基-2，5-二氧环戊基)戊烯-2-烯醛的一系列有机催化Michael-Michael-Aldol-Henry反应。产物的结构和绝对构型通过相应产物的X-射线分析得到确认。
An expedited method has been developed for the enantioselective synthesis of highly functionalized steroid systems containing six contiguous stereogenic centers with high enantioselectivities (99% ee). The one-pot methodology comprises a cascade of organocatalytic Michael-Michael-aldol-Henry reactions of 7-nitrohept-3-en-2-one and 5-(1-methyl-2,5-dioxocyclopentyl)pent-2-enal. The structure and absolute configuration of the products were confirmed by X-ray analyses of appropriate products.