A Unique Cascade Reaction between 3-Arylprop-2-inylcarboxylates and Benzaldehydes Leading to the Formation of Morita-Baylis-Hillman Adducts

被引:15
作者
Karpaviciene, Ieva [1 ]
Cikotiene, Inga [1 ]
机构
[1] Vilnius State Univ, Fac Chem, Dept Organ Chem, LT-03225 Vilnius, Lithuania
关键词
PHENYL VINYL KETONE; ALDEHYDES; ACRYLATE; THIOACRYLATE; DIMERIZATION; CATALYSIS; ALKYNES; BF3;
D O I
10.1021/ol303319a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
During an alkyne-carbonyl metathesis reaction between electron-rich 3-arylprop-2-inylcarboxylates and electron-poor benzaldehydes, a smooth migration of carboxylate groups takes place. This unique cascade reaction allows the formation of Morita-Baylis-Hillman (MBH) adducts unavailable via a traditional MBH reaction.
引用
收藏
页码:224 / 227
页数:4
相关论文
共 33 条
[1]   DABCO CATALYZED DIMERIZATION OF ALPHA,BETA-UNSATURATED KETONES AND NITRILES [J].
BASAVAIAH, D ;
GOWRISWARI, VVL ;
BHARATHI, TK .
TETRAHEDRON LETTERS, 1987, 28 (39) :4591-4592
[2]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[3]   Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry [J].
Basavaiah, Deevi ;
Reddy, Bhavanam Sekhara ;
Badsara, Satpal Singh .
CHEMICAL REVIEWS, 2010, 110 (09) :5447-5674
[4]  
Baylis A. B., 1972, German Pat, Patent No. 2155113
[5]   Regioselective Cyclizations Utilizing a Gold-Catalyzed [3,3] Propargyl Ester Rearrangement [J].
Cran, John W. ;
Krafft, Marie E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (37) :9398-9402
[6]   Ytterbium triflate promoted coupling reaction between aryl alkynes and aldehydes [J].
Curini, M ;
Epifano, F ;
Maltese, F ;
Rosati, O .
SYNLETT, 2003, (04) :552-554
[7]   aza-Baylis-Hillman Reaction [J].
Declerck, Valerie ;
Martinez, Jean ;
Lamaty, Frederic .
CHEMICAL REVIEWS, 2009, 109 (01) :1-48
[8]   Lewis acid promoted hetero [2+2] cycloaddition reactions of aldehydes with 10-propynyl-9(10H)-acridone.: A highly stereoselective synthesis of acrylic acid derivatives and 1,3-dienes using an electron deficient variant of ynamine [J].
Hsung, RP ;
Zificsak, CA ;
Wei, LL ;
Douglas, CJ ;
Xiong, H ;
Mulder, JA .
ORGANIC LETTERS, 1999, 1 (08) :1237-1240
[9]   A Practical Synthesis of Morita-Baylis-Hillman Adducts of Aryl Vinyl Ketones Catalyzed by a Proton Donor [J].
Kim, Sung Hwan ;
Kim, Se Hee ;
Lim, Cheol Hee ;
Kim, Jae Nyoung .
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (06) :2023-2027
[10]   Antiproliferative effect of Baylis-Hillman adducts and a new phthalide derivative on human tumor cell lines [J].
Kohn, Luciana K. ;
Pavam, C. H. ;
Veronese, D. ;
Coelho, F. ;
De Carvalho, J. E. ;
Almeida, Wanda P. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (06) :738-744