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J Am Chem Soc. 2010 Apr 14;132(14):5030-2. doi: 10.1021/ja101256v.

Enantioselective thiourea-catalyzed cationic polycyclizations.

Author information

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

Abstract

A new thiourea catalyst is reported for the enantioselective cationic polycyclization of hydroxylactams. Both the yield and enantioselectivity of this transformation were found to vary strongly with the identity of a single aromatic residue on a common catalyst framework, with more expansive and polarizable arenes proving optimal. Evidence is presented for a mechanism in which stabilizing cation-pi interactions are a principal determinant of enantioselectivity.

PMID:
20369901
PMCID:
PMC2989498
DOI:
10.1021/ja101256v
[Indexed for MEDLINE]
Free PMC Article

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