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.
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页数：5
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