Unnatural tripeptide as highly enantioselective organocatalyst for asymmetric aldol reaction of isatins

被引：15
|
作者：
Kon, Kazumasa [1 ]
Kohari, Yoshihito [2 ]
Murata, Miki [1 ,2 ]
机构：
[1] Kitami Inst Technol, Grad Sch Mfg Engn, 165 Koen Cho, Kitami, Hokkaido 0908507, Japan
[2] Kitami Inst Technol, Fac Engn, Sch Earth Energy & Environm Engn, 165 Koen Cho, Kitami, Hokkaido 0908507, Japan
来源：
TETRAHEDRON LETTERS | 2019年 / 60卷 / 05期
关键词：
Peptide; Organocatalyst; Aldol reaction; Isatins; Enantioselective; PROLINE-BASED DIPEPTIDES; TERT-BUTYL ESTERS; (S)-PROLINE-CONTAINING DIPEPTIDES; BIFUNCTIONAL ORGANOCATALYSTS; EFFICIENT ORGANOCATALYSTS; SMALL PEPTIDES; CATALYSTS; DERIVATIVES;
D O I：
10.1016/j.tetlet.2018.12.049
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The development of unnatural tripeptides as highly enantioselective organocatalysts for the asymmetric aldol reaction of isatins was achieved. H-Pro-Gly-D-Ala-OH with the D-alanine residue as the C-terminal amino acid residue expressed the best enantioselectivity. The H-Pro-Gly-D-Ala-OH-catalyzed reaction of isatins gave various aldol adducts with up to 93% yield and up to 97% ee. Investigation of the transition state via OFT calculation revealed that high optical purity was realized by the D-alanine controlled steric environment. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：415 / 418
页数：4
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