Enantioselective Thiourea-Catalyzed Cationic Polycyclizations

被引：253

作者：

Knowles, Robert R. ^{[1
]}

Lin, Song ^{[1
]}

Jacobsen, Eric N. ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 14期

关键词：

SQUALENE-HOPENE CYCLASE; PICTET-SPENGLER REACTIONS; PI-INTERACTIONS; AMINO-ACID; BIOMIMETIC CYCLIZATION; OXIDOSQUALENE CYCLASES; AROMATIC-HYDROCARBONS; POLYENE CYCLIZATION; FUNCTIONAL-ANALYSIS; ION-PAIR;

D O I：

10.1021/ja101256v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：5030 / +

页数：4

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