Dihedral angle restriction within a peptide-based tertiary alcohol kinetic resolution catalyst

被引：39

作者：

Angione, Mary C. ^{[1
]}

Miller, Scott J. ^{[1
]}

机构：

[1] Boston Coll, Dept Chem, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA

来源：

TETRAHEDRON | 2006年 / 62卷 / 22期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/j.tet.2006.01.104

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Kinetic resolution of several tertiary alcohols has been evaluated with a peptide-based catalyst that was designed to probe the role of dihedral angle restrictions for certain bonds within the catalyst. In particular, the nucleophilic residue (pi-Me)-His has been replaced with the (beta-Me)-(pi-Me)-His. A synthesis of the key residue is presented, along with characterization data that suggests the substituent exerts a substantial ground state conformational effect. In addition, kinetic resolution data indicate that the H- to Me-substitution confers enhanced stereoselectivity in several tertiary alcohol resolutions. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5254 / 5261

页数：8

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