Enantioselective Organocatalytic Synthesis of 1,2,3-Trisubstituted Cyclopentanes

被引：5

作者：

Sotolova, Martina ^{[1
]}

Kamlar, Martin ^{[1
]}

Remes, Marek ^{[1
]}

Geant, Pierre-Yves ^{[1
]}

Cisarova, Ivana ^{[2
]}

Sticha, Martin ^{[1
,3
]}

Vesely, Jan ^{[1
]}

机构：

[1] Charles Univ Prague, Fac Sci, Dept Organ Chem, Hlavova 2030-8, Prague 12800 2, Czech Republic

[2] Charles Univ Prague, Fac Sci, Dept Inorgan Chem, Hlavova 2030-8, Prague 12800 2, Czech Republic

[3] Charles Univ Prague, Fac Sci, Dept Chem, Hlavova 2030-8, Prague 12800 2, Czech Republic

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 36期

关键词：

Aminocatalysis; Asymmetric synthesis; Domino reaction; Enantioselectivity; Organocatalysis; MICHAEL/ALPHA-ALKYLATION REACTIONS; BOND-FORMING REACTIONS; ASYMMETRIC-SYNTHESIS; SUBSTITUTED CYCLOPENTANES; ALPHA-ALKYLATION; DOMINO REACTIONS; CONSTRUCTION; ALDOL; CASCADE; ALDEHYDES;

D O I：

10.1002/ejoc.202100841

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An organocatalytic asymmetric domino Michael/alpha-alkylation reaction between enals and non-stabilized alkyl halides has been developed. Chiral secondary amine catalyzed cyclization reaction of 1-bromo-3-nitropropane with alpha,beta-unsaturated aldehydes provides 1,2,3-trisubstituted cyclopentane carbaldehydes with high diastereo- (dr up to 8 : 1) and enantioselectivities (ee up to 96 %).

引用

页码：5080 / 5089

页数：10

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