An Unusual Diastereoselective Pictet-Spengler Reaction: Synthesis of Novel Tetrahydro-β-Carboline Glycosides

被引：3

作者：

Pradhan, Prasun K.

Nandi, Debkumar ^{[1
]}

Das Pradhan, Soma ^{[2
]}

Jaisankar, Parasuraman ^{[1
]}

Giri, V. S. ^{[1
]}

机构：

[1] Indian Inst Chem Biol, Dept Chem, Kolkata 700032, India

[2] Vidyasagar Univ, Dept Chem DDE, Midnapore 721102, India

来源：

SYNLETT | 2013年 / 24卷 / 01期

关键词：

Pictet-Spengler reaction; stereoselectivity; diastereoselectivity; stereocontrol; glycosides; imines; pi-stacking interactions; CONDENSATION; DERIVATIVES; OXEPANES;

D O I：

10.1055/s-0032-1317632

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unusual kinetic approach to the Pictet-Spengler reaction was investigated, in which L- or D-tryptophan methyl ester reacted with aldehydes of 1,2-O-cyclohexylidene-3-allyloxy-alpha-D-xylofuranose, yielding exclusively the cis or trans diastereomer of tetrahydro-beta-carboline glycoside, respectively, with complete stereocontrol.

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收藏

页码：85 / 89

页数：5

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