Synthesis of Polysubstituted Electron-Deficient Cyclobutane via Michael Addition and Oxidative Cyclization

被引：0

作者：

Wang, Guangyin ^{[1
]}

Lv, Xuliang ^{[1
]}

Weng, Xiaodi ^{[1
]}

Tang, Xuefeng ^{[2
]}

Rong, Xianhui ^{[2
]}

机构：

[1] PLA Univ Sci & Technol, Key Lab Sci & Technol Electromagnet Environm Eff, Nanjing 210007, Peoples R China

[2] PLA Univ Sci & Technol, Dept Sci Res, Nanjing 210007, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 33卷 / 07期

关键词：

cyclobutane; Michael addition; oxidative cyclization; CARBON BOND FORMATION; POLYVALENT IODINE; FRAGMENTATION REACTIONS; CYCLOADDITION REACTION; CLEAN OXIDATION; RING EXPANSION; DERIVATIVES; FACILE; DIASTEREOSELECTIVITY; CONSTRUCTION;

D O I：

10.6023/cjoc201304029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthetic method to polysubstituted electron-deficient cyclobutane from simple starting materials was developed. The key reactions were a Michael addition and an iodine(III)-mediated oxidative cyclization. The structure of product was confirmed by its single-crystal diffraction analysis. A tentative pathway for the oxidative cyclization was proposed.

引用

页码：1532 / 1535

页数：4

共 54 条

[1] Adam JM, 1999, ANGEW CHEM INT EDIT, V38, P2728, DOI 10.1002/(SICI)1521-3773(19990917)38:18<2728::AID-ANIE2728>3.0.CO
[2] 2-0
[3] Synthesis of the furanosteroidal antibiotic viridin
Anderson, EA
Alexanian, EJ
Sorensen, EJ
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (15) : 1998 - 2001
[4] Bach T, 1998, SYNTHESIS-STUTTGART, P683
[5] Acid-catalyzed Grob fragmentation reactions of acetonides derived from terpenes
Barluenga, J
Alvarez-Pérez, M
Wuerth, K
Rodríguez, F
Fañanás, FJ
[J]. ORGANIC LETTERS, 2003, 5 (06) : 905 - 908
[6] Synthetic and mechanistic studies of the retro-Claisen rearrangement 4. An application to the total synthesis of (+)-Laurenyne
Boeckman, RK
Zhang, J
Reeder, MR
[J]. ORGANIC LETTERS, 2002, 4 (22) : 3891 - 3894
[7] Carbon-carbon bond formation by radical addition-fragmentation reactions of O-alkylated enols
Cai, YD
Roberts, BP
Tocher, DA
Barnett, SA
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (17) : 2517 - 2529
[8] Highly enantioselective [2+2]-cycloaddition reactions catalyzed by a chiral aluminum bromide complex
Canales, Eda
Corey, E. J.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (42) : 12686 - +
[9] Fe-catalyzed highly selective ring expansion of alkynylcyclopropyl alkanols to cyclobutanols
Chen, Anjun
Lin, Riyuan
Liu, Qingjian
Jiao, Ning
[J]. CHEMICAL COMMUNICATIONS, 2009, (44) : 6842 - 6844
[10] SYNTHETIC APPLICATIONS OF INTRAMOLECULAR ENONE OLEFIN PHOTOCYCLOADDITIONS
CRIMMINS, MT
[J]. CHEMICAL REVIEWS, 1988, 88 (08) : 1453 - 1473

← 1 2 3 4 5 6 →