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J Am Chem Soc. 2012 Jul 25;134(29):11992-4. doi: 10.1021/ja305851h. Epub 2012 Jul 10.

Highly enantioselective proton-initiated polycyclization of polyenes.

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1
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.

Abstract

This report describes the synthesis of a range of chiral polycyclic molecules (tricyclic to pentacyclic) from achiral polyene precursors by enantioselective proton-initiated polycyclization promoted by the 1:1 complex of o,o'-dichloro-BINOL and SbCl(5). 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.

PMID:
22780430
DOI:
10.1021/ja305851h
[Indexed for MEDLINE]

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