Synthesis of phosphino oxazoline ligand libraries from amino acid and phosphino carboxylate building blocks

被引:72
作者
Gilbertson, SR [1 ]
Chang, CWT [1 ]
机构
[1] Washington Univ, Dept Chem, St Louis, MO 63130 USA
关键词
D O I
10.1021/jo981420y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A modular route to new phosphine-oxazoline ligands is reported. The ability of these ligands to asymmetrically catalyze the addition of dimethyl malonate to 1,3-diphenylprop-2-enyl acetate was investigated. The best of these Ligands gave a palladium complex which catalyzed the addition of dimethyl malonate to 1,3-diphenylprop-2-enyl acetate in a 99% yield and in 98% enantiomeric excess (Table 3, entry 11).
引用
收藏
页码:8424 / 8431
页数:8
相关论文
共 31 条
[1]   PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC SUBSTITUTION - A LIGAND DESIGN INCORPORATING STERIC AND ELECTRONIC EFFECTS [J].
ALLEN, JV ;
COOTE, SJ ;
DAWSON, GJ ;
FROST, CG ;
MARTIN, CJ ;
WILLIAMS, JMJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (15) :2065-2072
[2]   Combinatorial chemistry [J].
Borman, S .
CHEMICAL & ENGINEERING NEWS, 1998, 76 (14) :47-+
[3]   MECHANISTIC AND SYNTHETIC STUDIES IN CATALYTIC ALLYLIC ALKYLATION WITH PALLADIUM COMPLEXES OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE [J].
BROWN, JM ;
HULMES, DI ;
GUIRY, PJ .
TETRAHEDRON, 1994, 50 (15) :4493-4506
[4]   Discovery of chiral catalysts through ligand diversity: Ti-catalyzed enantioselective addition of TMSCN to meso epoxides [J].
Cole, BM ;
Shimizu, KD ;
Krueger, CA ;
Harrity, JPA ;
Snapper, ML ;
Hoveyda, AH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (15) :1668-1671
[5]   ASYMMETRIC PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION USING PHOSPHORUS-CONTAINING OXAZOLINE LIGANDS [J].
DAWSON, GJ ;
FROST, CG ;
WILLIAMS, JMJ .
TETRAHEDRON LETTERS, 1993, 34 (19) :3149-3150
[6]   Design, synthesis, and evaluation of small-molecule libraries [J].
Ellman, JA .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :132-143
[7]   SELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTION [J].
FROST, CG ;
HOWARTH, J ;
WILLIAMS, JMJ .
TETRAHEDRON-ASYMMETRY, 1992, 3 (09) :1089-1122
[8]   Synthesis of (dicyclohexylphosphino)serine, its incorporation into a dodecapeptide, and the coordination of rhodium [J].
Gilbertson, SR ;
Wang, XF .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) :434-435
[9]   VERSATILE BUILDING-BLOCK FOR THE SYNTHESIS OF PHOSPHINE-CONTAINING PEPTIDES - THE SULFIDE OF DIPHENYLPHOSPHINOSERINE [J].
GILBERTSON, SR ;
CHEN, GH ;
MCLOUGHLIN, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (10) :4481-4482
[10]   The combinatorial synthesis of chiral phosphine ligands [J].
Gilbertson, SR ;
Wang, XF .
TETRAHEDRON LETTERS, 1996, 37 (36) :6475-6478