Chiral phosphine-catalyzed asymmetric [4+1] annulation of polar dienes with allylic derivatives: Enantioselective synthesis of substituted cyclopentenes

被引：5

作者：

Li, Hanyuan ^{[1
]}

He, Zhengjie ^{[1
,2
]}

机构：

[1] Nankai Univ, Coll Chem, State Key Lab Elemento Organ Chem, 94 Weijin Rd, Tianjin 300071, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, 94 Weijin Rd, Tianjin 300071, Peoples R China

来源：

TETRAHEDRON LETTERS | 2021年 / 67卷

基金：

中国国家自然科学基金;

关键词：

Chiral phosphines; Allylic derivatives; Cyclopentenes; 4+1] annulation; Asymmetric catalysis; BAYLIS-HILLMAN CARBONATES; ALPHA; BETA-UNSATURATED IMINES; 3+2 CYCLOADDITIONS; ALLENOATES; CONSTRUCTION; QUATERNARY; OLEFINS; ALLENES; SPIROPYRAZOLONES;

D O I：

10.1016/j.tetlet.2021.152863

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chiral phosphine-catalyzed asymmetric [4 + 1] annulation reaction of polar 1,3-dienes and allylic derivatives is reported. Under the catalysis of P-chiral bicyclic phosphine (15 mol%), a series of 1,1-dicyano-2,4-diaryl-1,3-dienes (21 examples) readily undergo stereoselective [4 + 1] annulation reactions with allylic acetate under mild conditions, delivering enantio-enriched polysubstituted cyclopentenes in 49-89% yields and 51-98% ee. A plausible mechanism for the reaction is also discussed. (C) 2021 Elsevier Ltd. All rights reserved.

引用

页数：5

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