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

页码：3298 / 3302

页数：5

共 50 条

[1] Phosphine-Catalyzed (4+2) Annulation of Allenoates Bearing Acidic Hydrogen with 1,1-Dicyanoalkenes
Gao, Zhenzhen
Zhou, Xiaoming
Xie, Lei
Wang, Xuekun
Wang, Shiben
Liu, Honglei
Guo, Hongchao
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (10): : 7169 - 7174
[2] Phosphine-Catalyzed (4+2) Annulation of δ-Sulfonamido-Substituted Enones with 1,1-Dicyanoalkenes: Synthesis of Piperidine Derivatives
Liu, Min
Zhou, Leijie
Shi, Wangyu
Hu, Yimin
Liao, Jianning
Duan, Zeqing
Wang, Wei
Wu, Yongjun
Zheng, Bing
Guo, Hongchao
ORGANIC LETTERS, 2021, 23 (20) : 7703 - 7707
[3] Phosphine-catalyzed [4+2] annulation and vinylogous addition reactions between 1,4-dien-3-ones and 1,1-dicyanoalkenes
Zhou, Rong
Wang, Jianfang
Tian, Junjun
He, Zhengjie
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (04) : 773 - 781
[4] Catalytic Annulation of Diethyl Methylenecyclopropane-1,1-dicarboxylate with 1,1-Dicyanoalkenes
Suzuki, Itaru
Tsunoi, Shinji
Shibata, Ikuya
ORGANIC LETTERS, 2017, 19 (10) : 2690 - 2693
[5] Phosphine-Catalyzed (3+2) Annulation of δ-Hydroxyl Allenylic Alcohols with Pyrazolinone-Derived Ketimines
Chen, Xi
Duan, Zeqing
Liu, Min
Zheng, Bing
Zhang, Qi
Guo, Hongchao
CHEMISTRYSELECT, 2025, 10 (03):
[6] Addition of Reformatsky reagents to 1,1-dicyanoalkenes
Ding, Y
Zhao, ZB
Zhou, CM
TETRAHEDRON, 1997, 53 (08) : 2899 - 2906
[7] Addition of Reformatsky reagents to 1,1-dicyanoalkenes
Tetrahedron, 53 (08):
[8] Phosphine-Catalyzed (4+1) Annulation: Rearrangement of Allenylic Carbamates to 3-Pyrrolines through Phosphonium Diene Intermediates
Blank, Brian R.
Andrews, Ian P.
Kwon, Ohyun
CHEMCATCHEM, 2020, 12 (17) : 4352 - 4372
[9] Cyclodimerization of 1,1-dicyanoalkenes and arylidenecyanoacetates promoted by ytterbium diiodide
Su, WK
Yang, BB
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2003, 80 (03) : 163 - 165
[10] Catalytic Cycloaddition of 2-Methyleneaziridines with 1,1-Dicyanoalkenes
Takahashi, Hiroki
Yasui, Seiji
Tsunoi, Shinji
Shibata, Ikuya
ORGANIC LETTERS, 2014, 16 (04) : 1192 - 1195

← 1 2 3 4 5 →