Sc(OTf)3-catalyzed smooth tandem [3+2] cycloaddition/ring opening of donor-acceptor cyclopropane 1,1-diesters with enol silyl ethers

被引:61
作者
Fang, Jie [1 ]
Ren, Jun [1 ]
Wang, Zhongwen [1 ]
机构
[1] Nankai Univ, Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 30071, Peoples R China
基金
中国国家自然科学基金;
关键词
Tandem; Cyclopropane; Cycloaddition; Enol silyl ether; Ring opening;
D O I
10.1016/j.tetlet.2008.09.028
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalyzed by Lewis acids, donor-acceptor cyclopropane 1,1-diesters reacted with enol silyl ethers to afford 1,6-dicarbonyl compounds in moderate to excellent yields. This supplied a mild carbon-carbon bond-forming method from the ring opening of cyclopropanes. A smooth tandem [3+2] cycloaddition/ring opening process has been clearly proved by an independent experiment. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6659 / 6662
页数:4
相关论文
共 48 条
[11]   Donor-acceptor cyclopropanes as three-carbon components in a [4+3] cycloaddition reaction with 1,3-diphenylisobenzofuran [J].
Ivanova, Olga A. ;
Budynina, Ekaterina M. ;
Grishin, Yuri K. ;
Trushkov, Igor V. ;
Verteletskii, Pavel V. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (06) :1107-1110
[12]   Highly enantioselective and diastereoselective cycloaddition of cyclopropanes with nitrones and its application in the kinetic resolution of 2-substituted cyclopropane-1,1-dicarboxylates [J].
Kang, Yan-Biao ;
Sun, Xiu-Li ;
Tang, Yong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (21) :3918-3921
[13]   Scandium triflate catalyzed cycloaddition of imines with 1,1-cyclopropanediesters: efficient and diastereoselective synthesis of multisubstituted pyrrolidines [J].
Kang, YB ;
Tang, Y ;
Sun, XL .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (02) :299-301
[14]   TRANS-ANNULAR ALDOL CONDENSATIONS WITHIN MACROCYCLIC LACTONES - A NOVEL-APPROACH TO 8-MEMBERED CARBOCYCLIC RINGS [J].
KARIM, MR ;
SAMPSON, P .
TETRAHEDRON LETTERS, 1988, 29 (52) :6897-6900
[15]   GaCl3-Catalyzed insertion of diazene derivatives into the cyclopropane ring [J].
Korotkov, Vadim S. ;
Larionov, Oleg V. ;
Hoftneister, Anja ;
Magull, Joerg ;
de Meijere, Armin .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (20) :7504-7510
[16]   Ln(OTf)3-catalyzed insertion of aryl isocyanides into the cyclopropane ring [J].
Korotkov, Vadim S. ;
Larionov, Oleg V. ;
de Meijere, Armin .
SYNTHESIS-STUTTGART, 2006, 21 (21) :3542-3546
[17]   The chemistry of cyclopropanols [J].
Kulinkovich, OG .
CHEMICAL REVIEWS, 2003, 103 (07) :2597-2632
[18]   SYNTHESIS OF RACEMIC (E)-2,3-METHANOTYROSINE AND (Z)-2,3-METHANOTYROSINE - NEW CYCLOPROPANE ANALOGS OF TYROSINE [J].
MAPELLI, C ;
TUROCY, G ;
SWITZER, FL ;
STAMMER, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (01) :145-149
[19]   Synthesis of indolizines and benzoindolizines by annulation of donor-acceptor cyclopropanes with electron-deficient pyridines and quinolines [J].
Morra, Nicholas A. ;
Morales, Christian L. ;
Bajtos, Barbora ;
Wang, Xin ;
Jang, Hyosook ;
Wang, Jian ;
Yu, Ming ;
Pagenkopf, Brian L. .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2385-2390
[20]   Cascade reactions in total synthesis [J].
Nicolaou, K. C. ;
Edmonds, David J. ;
Bulger, Paul G. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (43) :7134-7186