Palladium-catalyzed carbonylative cyclization of Baylis-Hillman adducts. An efficient approach for the stereoselective synthesis of 3-alkenyl phthalides

被引:50
作者
Coelho, F
Veronese, D
Pavam, CH
de Paula, VI
Buffon, R
机构
[1] Univ Estadual Campinas, IQ DQI, BR-13084971 Campinas, SP, Brazil
[2] Lab Synth Nat Prod & Drugs, IQ DQI, BR-13084971 Campinas, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
Baylis-Hillman adducts; phthalides; cyclization; palladium;
D O I
10.1016/j.tet.2006.02.045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-mediated carbonylative cyclization reaction of Baylis-Hillman adducts is disclosed. This simple, efficient and straightforward sequence leads to the formation of an array of 3-alkenylphthalides with different substitution patterns on the aromatic ring, with good chemical yields and selectivities. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4563 / 4572
页数:10
相关论文
共 122 条
[71]   An alternative route to the synthesis of lignans intermediates [J].
Masunari, A ;
Ishida, E ;
Trazzi, G ;
Almeida, WP ;
Coelho, F .
SYNTHETIC COMMUNICATIONS, 2001, 31 (14) :2127-2136
[72]   An alternative approach to aminodiols from Baylis-Hillman adducts. Stereoselective synthesis of chloramphenicol, fluoramphenicol and thiamphenicol [J].
Mateus, CR ;
Coelho, F .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2005, 16 (3A) :386-396
[73]   Diastereoselectivity in heterogeneous catalytic hydrogenation of Baylis-Hillman adducts.: Total synthesis of (±)-sitophilate [J].
Mateus, CR ;
Feltrin, MP ;
Costa, AM ;
Coelho, F ;
Almeida, WP .
TETRAHEDRON, 2001, 57 (32) :6901-6908
[74]   HYDROGENATION OF SUBSTITUTED PHTHALIC ANHYDRIDES OVER PALLADIUM [J].
MCALEES, AJ ;
MCCRINDLE, R ;
SNEDDON, DW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (18) :2030-2036
[75]   REDUCTION OF SUBSTITUTED PHTHALIC ANHYDRIDES WITH SODIUM-BOROHYDRIDE [J].
MCALEES, AJ ;
MCCRINDLE, R ;
SNEDDON, DW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (18) :2037-2038
[76]   A NEW AEROBIC OXIDATION SYSTEM USING PD-CU CATALYSTS IN THE PRESENCE OF CO [J].
MIYAMOTO, M ;
MINAMI, Y ;
UKAJI, Y ;
KINOSHITA, H ;
INOMATA, K .
CHEMISTRY LETTERS, 1994, (07) :1149-1152
[77]   A convenient and highly regio and stereoselective method for the synthesis of (E)-3-alkylidene isobenzofuran-1(3H)-ones (phthalides) [J].
Mukhopadhyay, R ;
Kundu, NG .
TETRAHEDRON, 2001, 57 (46) :9475-9480
[78]  
NAPOLITANO E, 1985, SYNTHESIS-STUTTGART, P38
[79]   Baylis-Hillman adducts in rhodium-catalyzed 1,4-additions: unusual reactivity [J].
Navarre, L ;
Darses, S ;
Genet, JP .
CHEMICAL COMMUNICATIONS, 2004, (09) :1108-1109
[80]   Cyclic carbopalladation. A versatile synthetic methodology for the construction of cyclic organic compounds [J].
Negishi, EI ;
Coperet, C ;
Ma, SM ;
Liou, SY ;
Liu, F .
CHEMICAL REVIEWS, 1996, 96 (01) :365-393