Solid-phase synthesis of α-substituted proline hydantoins and analogs

被引：24

作者：

Alsina, J ^{[1
]}

Scott, WL ^{[1
]}

O'Donnell, MJ ^{[1
]}

机构：

[1] Indiana Univ Purdue Univ, Dept Chem, Indianapolis, IN 46202 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 17期

基金：

美国国家卫生研究院;

关键词：

alkylation; amino acid; combinatorial chemistry; cyclative cleavage; alpha; omega-dihaloalkanes; hydantoin; proline; solid-phase;

D O I：

10.1016/j.tetlet.2005.01.163

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The manual solid-phase preparation of racemic alpha-substituted bicyclic proline hydantoins and analogs, which can potentially contain up to four sites of structural diversity (ring size and substitution on the ring or at the ring fusion), is described. Key steps involved alkylation of aldimines of resin-bound amino acids with alpha,omega-dihaloalkanes and intramolecular displacement of the halide to generate alpha-substituted prolines and homologs. After formation of resin-bound ureas by reaction of these sterically-hindered secondary amines with isocyanates, base-catalyzed cyclization/cleavage yielded the desired hydantoin products. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3131 / 3135

页数：5

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