Enantioselective Thiourea-Catalyzed Cationic Polycyclizations
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- 7 April 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 132 (14) , 5030-5032
- https://doi.org/10.1021/ja101256v
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−π interactions are a principal determinant of enantioselectivity.Keywords
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