Phosphine-Catalyzed Tandem Annulation of Allenylic Alcohols with 1,1-Dicyanoalkenes

被引：12
|
作者：
Duan, Zeqing [1 ,2 ]
Liu, Min [1 ,2 ]
Zheng, Bing [1 ,2 ]
Tang, Yi [1 ,2 ]
Du, Juan [1 ,2 ]
Wang, Lei [3 ]
Yu, Songcheng [4 ]
Wu, Yongjun [4 ]
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] Nutrichem Co LTD, Beijing 102206, Peoples R China
[4] Zhengzhou Univ, Coll Publ Hlth, Zhengzhou 450001, Peoples R China
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 18期
关键词：
BAYLIS-HILLMAN CARBONATES; DELTA-ACETOXY ALLENOATES; ASYMMETRIC 3+2 ANNULATIONS; ENANTIOSELECTIVE SYNTHESIS; CYCLOADDITION REACTIONS; CHIRAL PHOSPHINES; FACILE SYNTHESIS; ALLENES; CONSTRUCTION; KETIMINES;
D O I：
10.1021/acs.orglett.3c01066
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The phosphine-catalyzed tandem annulation of allenylic alcohols with 1,1-dicyanoalkenes has been developed, giving various bicyclic tetrahydrocyclopentafuran derivatives in 40- 89% yields with moderate to excellent diastereoselectivities. The fused ring was furnished through a sequential (3 + 2) annulation/ nucleophilic addition reaction. The unusual nucleophilic addition of an alkoxide ion to a cyano group led to a formation of tetrahydrofuran ring having an imino substituent.
引用
收藏
页码：3298 / 3302
页数：5
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