Exoselective 1,3-Dipolar [3+6] Cycloaddition of Azomethine Ylides with 2-Acylcycloheptatrienes: Stereoselectivity and Mechanistic Insight

被引：46

作者：

He, Zhao-Lin ^{[1
]}

Sheong, Fu Kit ^{[3
]}

Li, Qing-Hua ^{[1
]}

Lin, Zhenyang ^{[3
]}

Wang, Chun-Jiang ^{[1
,2
]}

机构：

[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China

[2] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 230012, Peoples R China

[3] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 06期

关键词：

CATALYTIC ASYMMETRIC CONSTRUCTION; EFFICIENT CONSTRUCTION; FACILE ACCESS; PYRROLIDINES; ALKALOIDS; CENTERS; TROPONE; ESTER;

D O I：

10.1021/acs.orglett.5b00011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly exo-selective 1,3-dipolar [3 + 6] cycloaddition of azomethine ylides with 2-acylcycloheptatrienes was realized with a Cu(I)/(S,R-p)-PPF-NHMe complex as the catalyst, leading to a diverse range of bridged piperidines with multiple functionalities in good yield with excellent stereoselectivity control. Theoretical calculations indicated a stepwise mechanism for this exo-selective [3 + 6] annulation, which accounts for the remarkable feature of this annulation: all of the larger substituent groups occupy the axial positions in the six-membered chairlike conformation of the piperidine ring.

引用

页码：1365 / 1368

页数：4

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