First example of electrophile induced Baylis-Hillman reaction: a novel facile one-pot synthesis of indolizine derivatives

被引:71
作者
Basavaiah, D [1 ]
Rao, AJ [1 ]
机构
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India
关键词
D O I
10.1039/b211349j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Treatment of pyridine-2-carboxaldehyde with activated alkenes such as alkyl vinyl ketones and cyclic enones in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides a novel facile one-pot synthesis of indolizine derivatives, thus for the first time describing an electrophile induced Baylis-Hillman reaction.
引用
收藏
页码:604 / 605
页数:2
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共 25 条
[11]   Self-assisted tandem Michael-aldol reactions of α,β-unsaturated ketones with aldehydes [J].
Kataoka, T ;
Kinoshita, S ;
Kinoshita, H ;
Fujita, M ;
Iwamura, T ;
Watanabe, S .
CHEMICAL COMMUNICATIONS, 2001, (19) :1958-1959
[12]   An efficient approach to Aspidosperma alkaloids via [4+2] cycloadditions of aminosiloxydienes:: Stereocontrolled total synthesis of (±)-tabersonine.: Gram-scale catalytic asymmetric syntheses of (+)-tabersonine and (+)-16-methoxytabersonine.: Asymmetric syntheses of (+)-aspidospermidine and (-)-quebrachamine [J].
Kozmin, SA ;
Iwama, T ;
Huang, Y ;
Rawal, VH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (17) :4628-4641
[13]   Asymmetric synthesis of (-)-swainsonine, (+)-1,2-di-epi-swainsonine, and (+)-1,2,8-tri-epi-swainsonine [J].
Lindsay, KB ;
Pyne, SG .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (22) :7774-7780
[14]  
Nakanishi M, 2002, ANGEW CHEM INT EDIT, V41, P1934, DOI 10.1002/1521-3773(20020603)41:11<1934::AID-ANIE1934>3.0.CO
[15]  
2-F
[16]   INDOLIZINE DERIVATIVES .3. CYCLIZATION OF ALDOL PRODUCT OF 2-PYRIDINECARBALDEHYDE AND BETA-DIMETHYLAMINO (OR BETA-HYDROXY-) KETONES [J].
POHJALA, E .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1975, 29 (10) :1079-1084
[17]  
Renaud P, 2002, ANGEW CHEM INT EDIT, V41, P3460, DOI 10.1002/1521-3773(20020916)41:18<3460::AID-ANIE3460>3.0.CO
[18]  
2-6
[19]   ASYMMETRIC-SYNTHESIS .3. ENANTIOSPECIFIC SYNTHESIS OF THE NATURAL 3R, 5R, 9R (-) GEPHYROTOXIN-223 AB [J].
ROYER, J ;
HUSSON, HP .
TETRAHEDRON LETTERS, 1985, 26 (12) :1515-1518
[20]   New discovery in the traditional Baylis-Hillman reaction of arylaldehydes with methyl vinyl ketone [J].
Shi, M ;
Li, CQ ;
Jiang, JK .
CHEMICAL COMMUNICATIONS, 2001, (09) :833-834