Fe-BPsalan complex catalyzed highly enantioselective Diels-Alder reaction of alkylidene β-ketoesters

被引：6

作者：

Ping, Yuan-Ji ^{[1
]}

Zhou, Yi-Ming ^{[1
,2
,3
]}

Wu, Liang-Liang ^{[4
]}

Li, Zong-Rui ^{[1
]}

Gu, Xin ^{[1
]}

Wan, Xiao-Long ^{[1
]}

Xu, Zhen-Jiang ^{[1
]}

Che, Chi-Ming ^{[1
,4
,5
]}

机构：

[1] Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, 345 Lingling Rd, Shanghai 200032, Peoples R China

[2] Shanghai Normal Univ, Educ Minist, Key Lab Resource Chem, Shanghai 200234, Peoples R China

[3] Shanghai Normal Univ, Shanghai Key Lab Rare Earth Funct Mat, Shanghai 200234, Peoples R China

[4] Univ Hong Kong, Dept Chem, State Key Lab Synthet Chem, Pokfulam Rd, Hong Kong, Peoples R China

[5] HKU Shenzhen Inst Res & Innovat, Shenzhen 518057, Guangdong, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2021年 / 8卷 / 09期

基金：

中国国家自然科学基金;

关键词：

AT-METAL COMPLEXES; ALPHA; BETA-UNSATURATED 2-ACYL IMIDAZOLES; ASYMMETRIC CATALYSIS; CONJUGATE ADDITION; MICHAEL ADDITION; IRON CATALYSIS; CYCLOPENTADIENE; DERIVATIVES; ACTIVATION; CATION;

D O I：

10.1039/d1qo00158b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical, highly efficient iron-catalyzed asymmetric Diels-Alder reaction of various alkylidene beta-ketoesters with dienes was developed. Both cyclic and acyclic alkylidene beta-ketoesters underwent the reaction well with the Fe-BPsalan complex as the catalyst to afford the addition products including estrone analogues in excellent yields, good to high diastereoselectivities and excellent enantioselectivities under mild reaction conditions. DFT calculations revealed the critical role of the steric effect in directing the reaction selectivity.

引用

页码：1910 / 1917

页数：8

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