Enantioselective synthesis of a highly potent selective serotonin reuptake inhibitor. An application of imidazolidinone catalysis to the alkylation of indoles with an α,β-disubstituted α,β-unsaturated aldehyde

被引：120

作者：

King, HD ^{[1
]}

Meng, ZX ^{[1
]}

Denhart, D ^{[1
]}

Mattson, R ^{[1
]}

Kimura, R ^{[1
]}

Wu, DD ^{[1
]}

Gao, Q ^{[1
]}

Macor, JE ^{[1
]}

机构：

[1] Bristol Myers Squibb Co, Wallingford, CT 06492 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 16期

关键词：

D O I：

10.1021/ol051000c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The synthesis of the highly potent and selective serotonin reuptake inhibitor 1 (BMS-594726) is described. In the key construction step, an enantioselective alkylation of the indole nucleus with an a-branched alpha,beta-unsaturated aldehyde 7 was accomplished utilizing MacMillan's imidazolidinone catalyst 3b. A rationale is presented for the unexpected stereochemical result, as well as the novel reactivity of the alpha-branched substrate.

引用

页码：3437 / 3440

页数：4

共 15 条

[11] Neurochemical, pharmacokinetic, and behavioral effects of the novel selective serotonin reuptake inhibitor BMS-505130 [J].