Enantioselective Synthesis of Spirobarbiturate-Cyclohexenes through Phosphine-Catalyzed Asymmetric [4+2] Annulation of Barbiturate-Derived Alkenes with Allenoates

被引：90
|
作者：
Liu, Honglei [1 ]
Liu, Yang [1 ]
Yuan, Chunhao [1 ]
Wang, Guo-Peng [2 ,3 ]
Zhu, Shou-Fei [2 ,3 ]
Wu, Yang [1 ]
Wang, Bo [1 ]
Sun, Zhanhu [1 ]
Xiao, Yumei [1 ]
Zhou, Qi-Lin [2 ,3 ]
Guo, Hongchao [1 ]
机构：
[1] China Agr Univ, Dept Appl Chem, Beijing 100193, Peoples R China
[2] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[3] Nankai Univ, Inst Elementoorgan Chem, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 06期
关键词：
DIPEPTIDE-BASED PHOSPHINES; N-ACYL AMINOPHOSPHINES; 3+2 CYCLOADDITION; AMINO-ACID; CHIRAL PHOSPHINES; STEREOGENIC CENTERS; FORMAL SYNTHESES; CYCLIC IMINES; INHIBITORS; ALLENES;
D O I：
10.1021/acs.orglett.6b00239
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An enantioselective synthesis of pharmaceutically important spirobarbiturates has been achieved via spirocyclic chiral phosphine-catalyzed asymmetric [4 + 2] annulation of barbiturate-derived alkenes with allenoates. With the use of this tool, various spirobarbiturate-cyclohexenes are obtained in good to excellent yields with excellent diastereo- and enantioselectivities. A wide range of alpha-substituted allenoates and barbiturate-derived alkenes were tolerated.
引用
收藏
页码：1302 / 1305
页数：4
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