NHC-Catalyzed Reaction of Enals with Hydroxy Chalcones: Diastereoselective Synthesis of Functionalized Coumarins

被引:34
作者
Bhunia, Anup [1 ]
Patra, Atanu [1 ]
Puranik, Vedavati G. [2 ]
Biju, Akkattu T. [1 ]
机构
[1] CSIR Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India
[2] CSIR Natl Chem Lab, Ctr Mat Characterizat, Pune 411008, Maharashtra, India
关键词
STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; DIRECT ANNULATIONS; CONJUGATE UMPOLUNG; HOMOENOLATE;
D O I
10.1021/ol400562z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The N-heterocyclic carbene-catalyzed annulation of enals with 2'-hydroxy chalcones afford cyclopentane-fused coumarin derivatives with an excellent level of diastereocontrol. The reaction tolerates a broad range of functional groups; 25 examples are given, and a preliminary mechanistic investigation is provided.
引用
收藏
页码:1756 / 1759
页数:4
相关论文
共 40 条
[1]   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
[2]   Organocatalytic umpolung: N-heterocyclic carbenes and beyond [J].
Bugaut, Xavier ;
Glorius, Frank .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) :3511-3522
[3]   Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones [J].
Burstein, C ;
Glorius, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6205-6208
[4]   N-heterocyclic carbene-catalyzed conjugate umpolung for the synthesis of γ-butyrolactones [J].
Burstein, Christian ;
Tschan, Serena ;
Xie, Xiulan ;
Glorius, Frank .
SYNTHESIS-STUTTGART, 2006, (14) :2418-2439
[5]   Cooperative N-Heterocyclic Carbene/Lewis Acid Catalysis for Highly Stereoselective Annulation Reactions with Homoenolates [J].
Cardinal-David, Benoit ;
Raup, Dustin E. A. ;
Scheidt, Karl A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (15) :5345-+
[6]   Conversion of α,β-unsaturated aldehydes into saturated esters:: An umpolung reaction catalyzed by nucleophilic carbenes [J].
Chan, A ;
Scheidt, KA .
ORGANIC LETTERS, 2005, 7 (05) :905-908
[7]   Enantioselective, cyclopentene-forming annulations via NHC-catalyzed benzoin-oxy-cope reactions [J].
Chiang, Pei-Chen ;
Kaeobamrung, Juthanat ;
Bode, Jeffrey W. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (12) :3520-+
[8]  
Chiang PC, 2011, RSC CATAL SER, P399
[9]   Cooperative Lewis acid/N-heterocyclic carbene catalysis [J].
Cohen, Daniel T. ;
Scheidt, Karl A. .
CHEMICAL SCIENCE, 2012, 3 (01) :53-57
[10]  
Ding D., 2008, EUR J ORG CHEM, P4949