Phosphine-Catalyzed (3+2) Annulation of γ-Substituted Cinnamic Aldehyde-Derived Morita-Baylis-Hillman Carbonates through Remote Activation

被引：6
|
作者：
Ren, Yue [1 ,2 ]
Shi, Wangyu [1 ,2 ]
Tang, Yi [1 ,2 ]
Piao, Shixiang [1 ,2 ]
Yu, Songcheng [3 ]
Wu, Yongjun [3 ]
Guo, Hongchao [1 ,2 ]
机构：
[1] China Agr Univ, Dept Chem, Beijing 100193, Peoples R China
[2] China Agr Univ, Innovat Ctr Pesticide Res, Beijing 100193, Peoples R China
[3] Zhengzhou Univ, Coll Publ Hlth, Zhengzhou 450001, Peoples R China
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 40期
基金：
中国国家自然科学基金;
关键词：
MODIFIED ALLYLIC COMPOUNDS; MBH CARBONATES; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC CONSTRUCTION; SEQUENTIAL ANNULATION; CHIRAL PHOSPHINES; CYCLOADDITION; ADDUCTS; ACCESS; IMINES;
D O I：
10.1021/acs.orglett.3c02887
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of gamma-substituted Morita-Baylis-Hillman (MBH) carbonates were synthesized and subjected to phosphine-catalyzed annulations with electrophilic exocyclic alkenes, giving various valuable spirocyclopentenes in moderate to excellent yields with moderate to excellent diastereoselectivities. A large scope of MBH carbonates bearing gamma-hydrogen, alkenyl, and alkynyl substituents was well tolerated. The annulation unprecedentedly involves beta-, gamma-, and delta-carbons of MBH carbonates.
引用
收藏
页码：7374 / 7379
页数：6
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