Highly Enantioselective Proton-Initiated Polycyclization of Polyenes
Highly Enantioselective Proton-Initiated Polycyclization of Polyenes
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DOI：
10.1021/ja305851h
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发表时间：
2012-07-25
影响因子：
15
通讯作者：
Corey, E. J.
中科院分区：
文献类型：
--
作者：
Surendra, Karavadhi;Corey, E. J.
本报告描述了一系列的手性多环分子（三环到五环）的合成从非手性多烯前体的对映选择性质子引发的多环化促进的11配合物的o，o '-二氯-BINOL和氯化锑。卓越的收益率（CA。90%/形成的环）和对映选择性（20：1至50：1）。该方法是实用且有效的，因为手性配体既容易从R，R-或S，S-BINOL制备，又容易通过萃取从反应混合物中回收。
This report describes the synthesis of a range of chiral polycyclic molecules (tricyclic to pentacyclic) from achiral polyene precursors by enantio-selective proton-initiated polycyclization promoted by the 11 complex of o,o'-dichloro-BINOL and SbCl5. Excellent yields (ca. 90% per ring formed) and enantioselectivety (20:1 to 50:1) were obtained. The process is practical as well as efficient, because the chiral ligand is both readily prepared from R,R- or S,S-BINOL and easily recovered from the reaction mixture by extraction.