Palladimn(II)-catalyzed one-pot enantioselective synthesis of arylglycine derivatives from ethyl glyoxylate, p-toluenesulfonyl isocyanate and arylboronic acids

被引:53
作者
Dai, Huixiong [1 ]
Yang, Miao [1 ]
Lu, Xiyan [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
arylboronic acids; arylglycines; enantioselectivity; one-pot reaction; palladium;
D O I
10.1002/adsc.200700362
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A palladium (II)-catalyzed, one-pot enantioselective synthesis of arylglycine derivatives from ethyl glyoxylate, p-toluenesulfonyl isocyanate and arylboronic acids giving moderate to good yields and enantioselectivity has been developed. This reaction provides a convenient and efficient method for the synthesis of arylglycines.
引用
收藏
页码:249 / 253
页数:5
相关论文
共 24 条
[1]   MODE OF BINDING OF DIMETHYL-SULFOXIDE IN PLATINUM(II) AND PALLADIUM(II) CATIONIC COMPLEXES CONTAINING A CHELATED DIAMINE - X-RAY CRYSTAL-STRUCTURES OF (2,2'-BIPYRIDYL)CHLORO(DIMETHYL SULFOXIDE-O)PALLADIUM(II) TETRAFLUOROBORATE AND CHLORO(DIMETHYL SULPHOXIDE-S)(ETHYLENEDIAMINE)PALLADIUM(II) PERCHLORATEY [J].
ANNIBALE, G ;
CATTALINI, L ;
BERTOLASI, V ;
FERRETTI, V ;
GILLI, G ;
TOBE, ML .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1989, (07) :1265-1271
[2]   A FACILE PROCEDURE FOR THE SYNTHESIS OF N-(TOSYL) IMINO-2 ACETIC-ACID ESTERS, IMPORTANT ENOPHILES FOR THE DIRECT SYNTHESIS OF EXOTIC ALPHA-AMINO-ACIDS [J].
BAILLARGE, M ;
LEGOFFIC, F .
SYNTHETIC COMMUNICATIONS, 1987, 17 (13) :1603-1606
[3]   Asymmetric synthesis of protected arylglycines by rhodium-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters [J].
Beenen, Melissa A. ;
Weix, Daniel J. ;
Ellman, Jonathan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (19) :6304-6305
[4]   Diastereoselective synthesis of arylglycine derivatives by cationic Palladium(II)-Catalyzed addition of arylboronic acids to N-tert-Butanesulfinyl imino esters [J].
Dai, Huixiong ;
Lu, Xiyan .
ORGANIC LETTERS, 2007, 9 (16) :3077-3080
[5]   A novel synthesis of α-amino acid derivatives through catalytic, enantioselective ene reactions of α-imino esters [J].
Drury, WJ ;
Ferraris, D ;
Cox, C ;
Young, B ;
Lectka, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (42) :11006-11007
[6]   Catalytic, enantioselective alkylation of α-amino esters:: The synthesis of nonnatural α-amino acid derivatives [J].
Ferraris, D ;
Young, B ;
Cox, C ;
Dudding, T ;
Drury, WJ ;
Ryzhkov, L ;
Taggi, AE ;
Lectka, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (01) :67-77
[7]   Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts [J].
Ferraris, D ;
Young, B ;
Dudding, T ;
Lectka, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) :4548-4549
[8]  
HAMLEY P, 1991, SYNLETT, P29
[9]   Asymmetric Friedel-Crafts addition of indoles to N-sulfonyl aldimines:: A simple approach to optically active 3-indolyl-methanamine derivatives [J].
Jia, YX ;
Xie, JH ;
Duan, HF ;
Wang, LX ;
Zhou, QL .
ORGANIC LETTERS, 2006, 8 (08) :1621-1624
[10]   Palladium-bipyridine catalyzed conjugate addition of arylboronic acids to α,β-unsaturated carbonyl compounds in aqueous media [J].
Lin, Shaohui ;
Lu, Xiyan .
TETRAHEDRON LETTERS, 2006, 47 (40) :7167-7170