Microwave-accelerated asymmetric allylations using cysteine derived oxazolidine and thiazolidine palladium complexes

被引:30
作者
Braga, AL [1 ]
Silveira, CC
de Bolster, MWG
Schrekker, HS
Wessjohann, LA
Schneider, PH
机构
[1] Univ Fed Santa Maria, Dept Quim, BR-97105900 Santa Maria, RS, Brazil
[2] Free Univ Amsterdam, Dept Organ & Inorgan Chem, Fac Sci, Div Chem, NL-1081 HV Amsterdam, Netherlands
[3] Leibniz Inst Plant Biochem, D-06120 Halle An Der Saale, Germany
关键词
microwave; palladium; allylation; asymmetric catalysis; oxazolidine; thiazolidine;
D O I
10.1016/j.molcata.2005.06.008
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A set of enantiopure oxazolidine-thioether and thiazolidine-alcohol palladium complexes catalyze the microwave-mediated enantioselective allylation of rac-1,3-diphenyl-2-propenyl acetate with dimethyl malonate. Good yields and ee's were achieved in reaction times of 2 min instead of hours with conventional heating. (c) 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:235 / 238
页数:4
相关论文
共 25 条
[1]   New C2-symmetric chiral disulfide ligands derived from (R)-cysteine [J].
Braga, AL ;
Appelt, HR ;
Schneider, PH ;
Rodrigues, OED ;
Silveira, CC ;
Wessjohann, LA .
TETRAHEDRON, 2001, 57 (16) :3291-3295
[2]   A chiral disulfide derived from (R)-cysteine in the enantioselective addition of diethylzinc to aldehydes:: loading effect and asymmetric amplification [J].
Braga, AL ;
Lüdtke, DS ;
Wessjohann, LA ;
Paixao, MW ;
Schneider, PH .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 229 (1-2) :47-50
[3]   Facile and practical enantioselective synthesis of propargylic alcohols by direct addition of alkynes to aldehydes catalyzed by chiral disulfide-oxazolidine ligands [J].
Braga, AL ;
Appelt, HR ;
Silveira, CC ;
Wessjohann, LA ;
Schneider, PH .
TETRAHEDRON, 2002, 58 (52) :10413-10416
[4]   A new functionalized, chiral disulfide derived from L-cysteine:: (R,R)-bis[(3-benzyloxazolan-4-yl)-methane] disulfide as a catalyst in the diethylzinc addition to aldehydes [J].
Braga, AL ;
Appelt, HR ;
Schneider, PH ;
Silveira, CC ;
Wessjohann, LA .
TETRAHEDRON-ASYMMETRY, 1999, 10 (09) :1733-1738
[5]   Rapid microwave-induced palladium-catalyzed asymmetric allylic alkylation [J].
Bremberg, U ;
Larhed, M ;
Moberg, C ;
Hallberg, A .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1082-1083
[6]   Dielectric parameters relevant to microwave dielectric heating [J].
Gabriel, C ;
Gabriel, S ;
Grant, EH ;
Halstead, BSJ ;
Mingos, DMP .
CHEMICAL SOCIETY REVIEWS, 1998, 27 (03) :213-223
[7]  
Kuhnert N., 2002, ANGEW CHEM, V114, P1943
[8]   Microwave-accelerated homogeneous catalysis in organic chemistry [J].
Larhed, M ;
Moberg, C ;
Hallberg, A .
ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (09) :717-727
[9]   Microwave-assisted high-speed chemistry: a new technique in drug discovery [J].
Larhed, M ;
Hallberg, A .
DRUG DISCOVERY TODAY, 2001, 6 (08) :406-416
[10]   Microwave-promoted palladium-catalyzed coupling reactions [J].
Larhed, M ;
Hallberg, A .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9582-9584