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
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.
引用
收藏
页码:85 / 89
页数:5
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