Chiral VAPOL Imidodiphosphoric Acid-Catalyzed Asymmetric Vinylogous Mannich Reaction for the Synthesis of Butenolides

被引：5
作者：
Zhou, Tianyun [1 ,2 ]
Gao, Jigang [1 ]
Liu, Guofeng [1 ]
Guan, Xukai [1 ]
An, Dong [1 ]
Zhang, Suoqin [1 ,2 ]
Zhang, Guangliang [1 ]
机构：
[1] Jilin Univ, Coll Chem, 2699 Qianjin St, Changchun 130012, Jilin, Peoples R China
[2] Jilin Univ, Coll Life Sci, Minist Educ, Key Lab Mol Enzymol & Engn, 2699 Qianjin St, Changchun 130012, Jilin, Peoples R China
来源：
SYNLETT | 2018年 / 29卷 / 15期
关键词：
butenolides; trimethylsiloxyfuran; organocatalysis; enantioselectivity; asymmetric vinylogous Mannich reaction; FRIEDEL-CRAFTS REACTIONS; PHOSPHINE-OXAZOLINE LIGANDS; ALKYL-SUBSTITUTED ALDEHYDES; CONFINED BRONSTED ACIDS; ENANTIOSELECTIVE SYNTHESIS; PHOSPHORIC-ACID; CYCLIZATION REACTIONS; HIGHLY EFFICIENT; TRIMETHYLSILOXYFURAN; ACTIVATION;
D O I：
10.1055/s-0037-1610232
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chiral butenolides were synthesized by the enantioselective vinylogous Mannich reaction. Chiral (VAPOL)-type imidodiphosphoric acids are efficient catalysts for the asymmetric vinylogous Mannich (AVM) reaction of aldimines and trimethylsiloxyfuran in toluene. Under the optimized conditions, a series of butenolides were obtained with high yields (up to 98%) and enantioselectivities (up to 97% ee) as well as excellent diastereoselectivities (up to 99:1 dr).
引用
收藏
页码：2006 / 2010
页数：5
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