Synthesis of tryptophans by alkylation of chiral glycine enolate equivalents with quaternary gramines

被引：5

作者：

Reinfelds, Matiss ^{[1
]}

Kalinins, Konstantins ^{[1
]}

Katkevica, Dace ^{[1
]}

Zemribo, Ronalds ^{[1
]}

Katkevics, Martins ^{[1
]}

机构：

[1] Latvian Inst Organ Synth, LV-1006 Riga, Latvia

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 43期

关键词：

Gramine; Williams' morpholinone; Diastereoselective alkylation; Tryptophan; ALPHA-AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ANALOGS; DERIVATIVES;

D O I：

10.1016/j.tetlet.2015.09.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Quaternary gramines were found to be a suitable source of the 3-methylindole fragment for diastereoselective alkylation. The best yields and stereoselectivity were obtained for the alkylation of a chiral William's morpholinone enolate. Based on this transformation, a general method for the synthesis of enantiopure, indole ring substituted tryptophan derivatives was developed with good overall yields. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：5882 / 5885

页数：4

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