N,2,3,4-Tetrasubstituted Pyrrolidines through Tandem Lithium Amide Conjugate Addition/Radical Cyclization/Oxygenation Reactions

被引：10

作者：

Kafka, Frantisek ^{[1
]}

Pohl, Radek ^{[1
]}

Cisarova, Ivana ^{[2
]}

Mackman, Richard ^{[3
]}

Bahador, Gina ^{[3
]}

Jahn, Ullrich ^{[1
]}

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, Flemingovo Namesti 2, Prague 16610 6, Czech Republic

[2] Charles Univ Prague, Fac Sci, Dept Inorgan Chem, Albertov 6, Prague 12843 2, Czech Republic

[3] Gilead Sci Inc, 333 Lakeside Dr, Foster City, CA 94404 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 22期

关键词：

Tandem reactions; Nitrogen heterocycles; Michael addition; Radical reactions; Cyclization; Enolates; CATALYZED RADICAL REACTIONS; O-IODOXYBENZOIC ACID; ASYMMETRIC-SYNTHESIS; CYCLOPENTANE DERIVATIVES; AMMONIA EQUIVALENTS; EFFICIENT STRATEGY; FERROCENIUM SALTS; PART; CYCLIZATION; PIPERIDINE;

D O I：

10.1002/ejoc.201600621

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective syntheses of densely functionalized pyrrolidines deriving their chirality from (R)-1-(phenyl) ethylamine are reported. Allylic amines and beta-substituted-alpha, beta-unsaturated esters are used as the building blocks in this one-pot reaction. Single electron transfer (SET) oxidation served to merge the reactivities of anionic enolate and radical intermediates. Ferrocenium hexafluorophosphate, which is easy to prepare, store and handle, was applied as SET oxidant and persistent free radical TEMPO served as the oxygenating agent introducing a protected hydroxy function, which proved to be beneficial for further derivatization. Exclusive 2,3-trans and up to 6: 1 3,4-cis/trans diastereoselectivities were achieved in the targeted tetrasubstituted pyrrolidines.

引用

页码：3862 / 3871

页数：10

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