Mechanistic switch leading to highly efficient chirality transfer in Pd(0)-catalyzed coupling-cyclization of aryl iodides with 1:1 acid-base salts of 2,3-allenoic acids and L-(-)-cinchonidine or D-(+)-/L-(-)-α-methylbenzylamine.: Enantioselective synthesis of highly optically active 3-aryl polysubstituted butenolides

被引:52
作者
Ma, SM [1 ]
Shi, ZJ [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1039/b109645a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient methodology provides an easy access to highly optically active polysubstituted butenolides starting from aryl halides and 1:1 salts of optically active 2,3-allenoic acid-base via an oxidative addition-coordinative cyclization-reductive elimination mechanism, which led to the high efficiency of this chirality isomerization reaction.
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页码:540 / 541
页数:2
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共 32 条
[1]   Brief syntheses of (+)-blastmycinone and related γ-lactones from an asymmetrically dihydroxylated carboxylic ester [J].
Berkenbusch, T ;
Bruckner, R .
TETRAHEDRON, 1998, 54 (38) :11461-11470
[2]   REAKTIONEN MIT PHOSPHINALKYLENEN .12. EINE NEUE SYNTHESE VON ALLEN-CARBONSAUREESTERN [J].
BESTMANN, HJ ;
HARTUNG, H .
CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (04) :1198-&
[3]  
Brima T. S., 1990, US Pat, Patent No. [4968817, 4968817A]
[4]   Fissohamione, a novel furanone from Fissistigma oldhamii [J].
Chia, YC ;
Chang, FR ;
Wu, YC .
TETRAHEDRON LETTERS, 1999, 40 (42) :7513-7514
[5]   Meliacin butenolides from Trichilia estipulata [J].
Cortez, DAG ;
Fernandes, JB ;
Vieria, PC ;
Da Silva, MFGF ;
Ferreira, AG ;
Cass, QB ;
Pirani, JR .
PHYTOCHEMISTRY, 1998, 49 (08) :2493-2496
[6]   Synthesis of (+)- and (-)-phaseolinic acid by combination of enzymatic hydrolysis and chemical transformations with revision of the absolute configuration of the natural product [J].
Drioli, S ;
Felluga, F ;
Forzato, C ;
Nitti, P ;
Pitacco, G ;
Valentin, E .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) :2385-2388
[7]  
Gauthier J.Y., 1995, PCT Int. Appl. WO 95 00,501, Patent No. [9500501, 95 00,501]
[8]  
Guo SJ, 1997, INDIAN J CHEM B, V36, P339
[9]  
Hashmi ASK, 2000, ANGEW CHEM INT EDIT, V39, P3590
[10]   Cochinolide, a new γ-alkylidene bicyclic butenolide with antiviral activity, and its β-glucopyranoside from Homalium cochinchinensis [J].
Ishikawa, T ;
Nishigaya, K ;
Uchikoshi, H ;
Chen, IS .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (04) :534-537