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

页码：1302 / 1305

页数：4

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