Fe-catalyzed highly selective ring expansion of alkynylcyclopropyl alkanols to cyclobutanols

被引：33
作者：
Chen, Anjun [1 ,2 ]
Lin, Riyuan [1 ]
Liu, Qingjian [2 ]
Jiao, Ning [1 ,3 ]
机构：
[1] Peking Univ, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
[2] Shandong Normal Univ, Dept Chem, Jinan 250014, Peoples R China
[3] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2009年 / 44期
基金：
美国国家科学基金会;
关键词：
C BOND ACTIVATION; CYCLOADDITION REACTIONS; BUILDING-BLOCKS; IRON; METAL; METHYLENECYCLOPROPANES; CYCLOISOMERIZATION; VINYLCYCLOPROPANES; REARRANGEMENT; DERIVATIVES;
D O I：
10.1039/b916623h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A Fe-catalytic highly selective ring expansion reaction of alkynylcyclopropyl alkanols to alkynylcyclobutanols via a 1,2-carbon shift under mild conditions was developed. A new class of homogeneous FeCl2/O-2 catalytic system was employed in these novel transformations.
引用
收藏
页码：6842 / 6844
页数：3
相关论文
共 59 条
[1]   Thermal rearrangements of vinylcyclopropanes to cyclopentenes [J].
Baldwin, JE .
CHEMICAL REVIEWS, 2003, 103 (04) :1197-1212
[2]   Gif chemistry: The present situation [J].
Barton, DHR .
TETRAHEDRON, 1998, 54 (22) :5805-5817
[3]   Iron-catalyzed reactions in organic synthesis [J].
Bolm, C ;
Legros, J ;
Le Paih, J ;
Zani, L .
CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254
[4]   Heterocycles from alkylidenecyclopropanes [J].
Brandi, A ;
Cicchi, S ;
Cordero, FM ;
Goti, A .
CHEMICAL REVIEWS, 2003, 103 (04) :1213-1269
[5]   Development of a Formal [4+1] Cycloaddition: Pd(OAc)2-Catalyzed Intramolecular Cyclopropanation of 1,3-Dienyl β-Keto Esters and MgI2-Promoted Vinylcyclopropane-Cyclopentene Rearrangement [J].
Coscia, Rockford W. ;
Lambert, Tristan H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (07) :2496-+
[6]   Introduction: Cyclopropanes and related rings [J].
de Meijere, A .
CHEMICAL REVIEWS, 2003, 103 (04) :931-932
[7]  
de Meijere A., 1996, CARBOCYCLIC 3 MEMB A, VE17a-c
[8]   Sustainable metal catalysis with iron: From rust to a rising star? [J].
Enthaler, Stephan ;
Junge, Kathrin ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (18) :3317-3321
[9]   Formation of five-membered carbocycles by intramolecular palladium-catalyzed ring opening of tert-cyclobutanols [J].
Ethirajan, Manivannan ;
Oh, Heong-Sub ;
Cha, Jin Kun .
ORGANIC LETTERS, 2007, 9 (14) :2693-2696
[10]   A cheap metal for a "Noble" task:: Preparative and mechanistic aspects of cycloisomerization and cycloaddition reactions catalyzed by low-valent iron complexes [J].
Fuerstner, Alois ;
Majima, Keisuke ;
Martin, Ruben ;
Krause, Helga ;
Kattnig, Egmont ;
Goddard, Richard ;
Lehmann, Christian W. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (06) :1992-2004
123456