The Baylis-Hillman reaction: a novel concept for creativity in chemistry

被引:319
作者
Basavaiah, Deevi [1 ]
Veeraraghavaiah, Gorre [1 ]
机构
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India
关键词
FRIEDEL-CRAFTS REACTION; ENANTIOSELECTIVE SYNTHESIS; CLAISEN-REARRANGEMENT; CATALYZED REACTION; REACTION-MECHANISM; ACRYLIC COMPOUNDS; FACILE SYNTHESIS; ADDUCTS; CONSTRUCTION; ESTERS;
D O I
10.1039/c1cs15174f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This tutorial review highlights the way in which the Baylis-Hillman reaction has been increasingly attracting the attention of synthetic and medicinal chemists; it not only helps in originating new ideas to create novel methodologies and molecules but also offers intellectual challenges to understand and address the present day needs in the areas of organic and medicinal chemistry.
引用
收藏
页码:68 / 78
页数:11
相关论文
共 91 条
[41]   Construction of Chiral Quaternary Carbon through Morita-Baylis-Hillman Reaction: An Enantioselective Approach to 3-Substituted 3-Hydroxyoxindole Derivatives [J].
Guan, Xiao-Yang ;
Wei, Yin ;
Shi, Min .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (46) :13617-13621
[42]   Chiral activated Alkenes induced asymmetric Baylis-Hillman reaction in Me3N/H2O/solvent medium [J].
He, Ke ;
Zhou, Zhenghong ;
Zhao, Guofeng ;
Tang, Chuchi .
HETEROATOM CHEMISTRY, 2006, 17 (04) :317-321
[43]   Chiral bifunctional N-heterocyclic carbenes: Synthesis and application in the aza-Morita-Baylis-Hillman reaction [J].
He, Lin ;
Zhang, Yan-Rong ;
Huang, Xue-Liang ;
Ye, Song .
SYNTHESIS-STUTTGART, 2008, (17) :2825-2829
[44]   MECHANISM OF ALPHA-SUBSTITUTION REACTIONS OF ACRYLIC DERIVATIVES [J].
HILL, JS ;
ISAACS, NS .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1990, 3 (05) :285-288
[45]   RCM-based approach to seven- and eight-member ring-fused β-carbolines [J].
Hutait, Samiran ;
Batra, Sanjay .
TETRAHEDRON LETTERS, 2010, 51 (44) :5781-5783
[46]   Enantio- and diastereocontrolled synthesis of an angular triquinane sesquiterpene (+)-arnicenone [J].
Iura, Y ;
Sugahara, T ;
Ogasawara, K .
ORGANIC LETTERS, 2001, 3 (02) :291-293
[47]   An enantio- and stereocontrolled synthesis of (-)-mycestericin E via cinchona alkaloid-catalyzed asymmetric Baylis-Hillman reaction [J].
Iwabuchi, Y ;
Furukawa, M ;
Esumi, T ;
Hatakeyama, S .
CHEMICAL COMMUNICATIONS, 2001, (19) :2030-2031
[48]   Chiral amine-catalyzed asymmetric Baylis-Hillman reaction:: A reliable route to highly enantiomerically enriched (α-methylene-β-hydroxy)esters [J].
Iwabuchi, Y ;
Nakatani, M ;
Yokoyama, N ;
Hatakeyama, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) :10219-10220
[49]   Reexamination of products and the reaction mechanism of the chalcogeno-Baylis-Hillman reaction:: Chalcogenide-TiCl4-mediated reactions of electron-deficient alkenes with aldehydes [J].
Kataoka, T ;
Kinoshita, H ;
Iwama, T ;
Tsujiyama, S ;
Iwamura, T ;
Watanabe, S ;
Muraoka, O ;
Tanabe, G .
TETRAHEDRON, 2000, 56 (27) :4725-4731
[50]   Synthesis of dihydroindenofuran scaffold via a Pd-catalyzed 5-endo-trig cyclization/enolate O-alkylation cascade [J].
Kim, Eun Sun ;
Kim, Ko Hoon ;
Park, Sunhong ;
Kim, Jae Nyoung .
TETRAHEDRON LETTERS, 2010, 51 (35) :4648-4652