Ring-Opening 1,3-Dichlorination of Donor-Acceptor Cyclopropanes by Iodobenzene Dichloride

被引:105
作者
Garve, Lennart K. B. [1 ]
Barkawitz, Philip [1 ]
Jones, Peter G. [1 ]
Werz, Daniel B. [1 ]
机构
[1] Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Chem, D-38106 Braunschweig, Germany
关键词
SUBSTITUTED CYCLOPROPANES; 3+2 CYCLOADDITION; 1,2-CYCLOPROPANATED SUGARS; ASYMMETRIC-SYNTHESIS; AMINOCYCLOPROPANES; ALDEHYDES; ANNULATION; FURAN; TETRAHYDROFURANS; REARRANGEMENTS;
D O I
10.1021/ol5029139
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Donor-acceptor cyclopropanes are reacted with iodobenzene dichloride to afford ring-opened products bearing chlorine atoms in the 1- and 3-positions, adjacent to the donor and acceptor groups. A variety of different donors (e.g., alkyl, aryl, N, and O) and acceptor moieties (e.g., ketones, diesters, and dinitriles) are used.
引用
收藏
页码:5804 / 5807
页数:4
相关论文
共 53 条
[1]   Silylmethyl-substituted cyclopropyl and other strained ring systems: cycloaddition with dipolarophiles [J].
Agrawal, Divya ;
Yadav, Veejendra K. .
CHEMICAL COMMUNICATIONS, 2008, (48) :6471-6488
[2]  
[Anonymous], 2015, Acta Crystallogr., V71, P3
[3]  
[Anonymous], 2013, VERSION 11713628
[4]   Catalytic Enantiospecific [3+2] Annulation of Aminocyclopropanes with Ketones [J].
Benfatti, Fides ;
de Nanteuil, Florian ;
Waser, Jerome .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (16) :4844-4849
[5]   Synthesis of [n,5]-Spiroketals by Ring Enlargement of Donor-Acceptor-Substituted Cyclopropane Derivatives [J].
Brand, Christian ;
Rauch, Gesche ;
Zanoni, Michele ;
Dittrich, Birger ;
Werz, Daniel B. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22) :8779-8786
[6]   THIOPHENE DERIVATIVES BY NOVEL REARRANGEMENTS OF SILOXY-SUBSTITUTED CYCLOPROPANECARBOXYLATES [J].
BRUCKNER, C ;
REISSIG, HU .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (07) :588-589
[7]   Heterocycles from cyclopropanes: applications in natural product synthesis [J].
Carson, Cheryl A. ;
Kerr, Michael A. .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3051-3060
[8]   Intramolecular donor-acceptor cyclopropane ring-opening cyclizations [J].
Cavitt, Marchello A. ;
Phun, Lien H. ;
France, Stefan .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (03) :804-818
[9]  
De Dimone F., 2009, SYNTHESIS-STUTTGART, P3353
[10]   Catalytic Friedel-Crafts Reaction of Aminocyclopropanes [J].
de Nanteuil, Florian ;
Loup, Joachim ;
Waser, Jerome .
ORGANIC LETTERS, 2013, 15 (14) :3738-3741