Lewis acid catalyzed [2+2] cycloaddition of ynamides and propargyl silyl ethers: synthesis of alkylidenecyclobutenones and their reactivity in ring-opening and ring expansion

被引：20

作者：

Chen, Ling ^{[1
]}

Cao, Jian ^{[1
]}

Xu, Zheng ^{[1
]}

Zheng, Zhan-Jiang ^{[1
]}

Cui, Yu-Ming ^{[1
]}

Xu, Li-Wen ^{[1
,2
]}

机构：

[1] Hangzhou Normal Univ, Key Lab Organosilicon Chem & Mat Technol, Minist Educ, 1378 Wenyi West Rd,Sci Pk HZNU, Hangzhou 311121, Zhejiang, Peoples R China

[2] Chinese Acad Sci, State Key Lab Oxo Synth & Select Oxidat, LICP, Beijing 100864, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 61期

基金：

中国国家自然科学基金;

关键词：

ORGANIC-SYNTHESIS; BOND ACTIVATION; ENE-YNAMIDES; DERIVATIVES; CYCLOBUTENONES; KETENES; BENZOCYCLOBUTENONES; CYCLOISOMERIZATIONS; BENZANNULATION; ALLENYLKETENES;

D O I：

10.1039/c6cc04648g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A family of four-membered enones, polysubstituted alkylidenecyclo-butenones, were easily prepared by a Lewis acid catalyzed [2+2] cycloaddition of ynamides and propargyl silyl ethers. This challenging regioselective [2+2] cycloaddition enables the efficient construction and conversion of four-membered enones, which provides high-value and structurally diverse products through the unexpected ring-opening and ring expansion of alkylidenecyclobutenone with Grignard reagents, organolithium, primary amines, and water.

引用

页码：9574 / 9577

页数：4

共 50 条

[41] AMINE CATALYZED RING-OPENING OF (2+2) CYCLOADDUCTS DERIVED FROM ENAMINES OF CYCLIC-KETONES AND METHYL PROPYNOATE
EGBERINK, RJM
VERBOOM, W
BENDERS, PH
HARKEMA, S
REINHOUDT, DN
RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1988, 107 (05): : 388 - 392
[42] Gadolinium Photocatalysis: Dearomative [2+2] Cycloaddition/Ring-Expansion Sequence with Indoles
Ma, Jiajia
Schaefers, Felix
Daniliuc, Constantin
Bergander, Klaus
Strassert, Cristian A.
Glorius, Frank
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (24) : 9639 - 9645
[43] A mild procedure for the Lewis acid-catalyzed ring-opening of activated cyclopropanes with amine nucleophiles
Lifchits, Olga
Charette, Andre B.
ORGANIC LETTERS, 2008, 10 (13) : 2809 - 2812
[44] Transition Metal/Lewis Acid Co-Catalyzed Ring-Opening Reactions of Oxa/Azabenzonorbornadienes
Zhang, Danni
Khan, Ruhima
Fan, Baomin
CHEMISTRYSELECT, 2020, 5 (19): : 5526 - 5536
[45] Lewis acid catalyzed ring-opening reactions of methylenecyclopropanes with diphenylphosphine oxide in the presence of sulfur or selenium
Shi, Min
Jiang, Min
Liu, Le-Ping
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (03) : 438 - 440
[46] Lewis acid-catalyzed ring-opening reactions of semicyclic N,O-acetals
Sugiura, M
Kobayashi, S
ORGANIC LETTERS, 2001, 3 (03) : 477 - 480
[47] Lewis Acid Catalyzed Cycloaddition of Bicyclobutanes with Ynamides for the Synthesis of Polysubstituted 2-Amino-bicyclo[2.1.1]hexenes
Hu, Qian-Qian
Wang, Liu-Yang
Chen, Xing-Hao
Geng, Ze-Xiang
Chen, Jie
Zhou, Ling
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (32)
[48] Synthesis of Cyclobutanones by Gold(I)-Catalyzed [2+2] Cycloaddition of Ynol Ethers with Alkenes
Zanini, Margherita
Cataffo, Andrea
Echavarren, Antonio M.
ORGANIC LETTERS, 2021, 23 (22) : 8989 - 8993
[49] Facile Synthesis of Trisubstituted Carbazoles by Acid-Catalyzed Ring-Opening Annulation of 2-Amidodihydrofurans with Indoles
Zhao, Jingjing
Li, Pan
Xia, Chungu
Li, Fuwei
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (46) : 16383 - 16386
[50] RING-OPENING SILYLFORMYLATION OF OXETANES CATALYZED BY [RHCL(CO)(2)](2)-AMINE
FUKUMOTO, Y
YAMAGUCHI, S
CHATANI, N
MURAI, S
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 489 (1-2) : 215 - 219

← 1 2 3 4 5 →