Proline catalyzed, one-pot three component Mannich reaction and sequential cyclization toward the synthesis of 2-substituted piperidine and pyrrolidine alkaloids

被引：8

作者：

Chacko, Shibin ^{[1
]}

Ramapanicker, Ramesh ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 15期

关键词：

Multicomponent reaction; Organocatalysis; Pyrrolidine; Piperidine; Mannich reaction; ENANTIOSELECTIVE SYNTHESIS; MULTICOMPONENT REACTIONS; ASYMMETRIC-SYNTHESIS; FORMAL SYNTHESIS; 3-COMPONENT; DERIVATIVES; ALDOL; ACCESS; ESTERS;

D O I：

10.1016/j.tetlet.2015.03.001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A very effective one-pot three component reaction of 4-bromobutanal or 5-bromopentanal, acetone, and p-anisidine catalyzed by proline is reported. A three component Mannich reaction followed by cyclization leading to the synthesis of 2-substituted pyrrolidine and piperidine derivatives through simultaneous formation of two C-N and one C-C bond is reported. The usefulness of the reaction is demonstrated by the synthesis of (+/-)coniine, (+/-)pelletrine, (+/-)sedridine, and (+/-)allosedridine. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：2023 / 2026

页数：4

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