N-heterocyclic carbene cascade catalysis: Dual Bronsted/Lewis base rearrangement of cyclopropyl enol esters to dihydropyranones

被引：66
作者：
Candish, Lisa [1 ]
Lupton, David W. [1 ]
机构：
[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia
来源：
CHEMICAL SCIENCE | 2012年 / 3卷 / 02期
基金：
澳大利亚研究理事会;
关键词：
DIELS-ALDER REACTIONS; ALPHA; BETA-UNSATURATED ALDEHYDES; MICHAEL ADDITION; TRANSESTERIFICATION/ACYLATION REACTIONS; ENANTIOSELECTIVE SYNTHESIS; COOPERATIVE CATALYSIS; ORGANIC-SYNTHESIS; VINYL SULFONES; GAMMA-LACTAMS; ORGANOCATALYSTS;
D O I：
10.1039/c1sc00666e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first example of Bronsted/Lewis base cascade catalysis using an N-heterocyclic carbene has been realised through the rearrangement of cyclopropyl esters to dihydropyranones. The scope and mechanism of this transformation has been examined implicating a novel NHC-mediated electrocyclic cyclopropane rearrangement followed by an anionic oxy Claisen-rearrangement.
引用
收藏
页码：380 / 383
页数：4
相关论文
共 70 条
[1]   A Simple Recipe for Sophisticated Cocktails: Organocatalytic One-Pot Reactions-Concept, Nomenclature, and Future Perspectives [J].
Albrecht, Lukasz ;
Jiang, Hao ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8492-8509
[2]   Preparation of a super bulky silver N-heterocyclic carbene complex [J].
Alexander, Sean G. ;
Cole, Marcus L. ;
Morris, Jonathan C. .
NEW JOURNAL OF CHEMISTRY, 2009, 33 (04) :720-724
[3]   INVESTIGATION OF BASE-CATALYZED ENOLIZATION OF CYCLOPROPYL KETONES [J].
AMBURN, HW ;
KAUFFMAN, KC ;
SHECHTER, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (02) :530-&
[4]   N-Heterocyclic Carbene-Promoted Rauhut-Currier Reactions between Vinyl Sulfones and α,β-Unsaturated Aldehydes [J].
Atienza, Roxanne L. ;
Scheidt, Karl A. .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2011, 64 (08) :1158-1164
[5]   N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones [J].
Atienza, Roxanne L. ;
Roth, Howard S. ;
Scheidt, Karl A. .
CHEMICAL SCIENCE, 2011, 2 (09) :1772-1776
[6]   IPr* an easily accessible highly hindered N-heterocyclic carbene [J].
Berthon-Gelloz, Guillaume ;
Siegler, Maxime A. ;
Spek, Anthony L. ;
Tinant, Bernard ;
Reek, Joost N. H. ;
Marko, Istvan E. .
DALTON TRANSACTIONS, 2010, 39 (06) :1444-1446
[7]   N-Heterocyclic Carbene Catalyzed Umpolung of Michael Acceptors for Intermolecular Reactions [J].
Biju, Akkattu T. ;
Padmanaban, Mohan ;
Wurz, Nathalie E. ;
Glorius, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (36) :8412-8415
[8]   Extending NHC-Catalysis: Coupling Aldehydes with Unconventional Reaction Partners [J].
Biju, Akkattu T. ;
Kuhl, Nadine ;
Glorius, Frank .
ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (11) :1182-1195
[9]   ON THE MECHANISM OF THIAMINE ACTION .4. EVIDENCE FROM STUDIES ON MODEL SYSTEMS [J].
BRESLOW, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (14) :3719-3726
[10]   Concepts of nature in organic synthesis: Cascade catalysis and multistep conversions in concert [J].
Bruggink, A ;
Schoevaart, R ;
Kieboom, T .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (05) :622-640
1234567