Diastereoselective synthesis of arylglycine derivatives by cationic Palladium(II)-Catalyzed addition of arylboronic acids to N-tert-Butanesulfinyl imino esters

被引:87
作者
Dai, Huixiong [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
D O I
10.1021/ol0711220
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A cationic palladium-complex-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl iminoacetates to yield the optically active arylglycine derivatives with moderate to good yield and high diastereoselectivity was developed. This reaction provides a convenient and efficient method for the synthesis of arylglycine derivatives.
引用
收藏
页码:3077 / 3080
页数:4
相关论文
共 37 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]   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
[3]   Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].
Bloch, R .
CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438
[4]   A room-temperature protocol for the rhodium(I)-catalyzed addition of arylboron compounds to sulfinimines [J].
Bolshan, Y ;
Batey, RA .
ORGANIC LETTERS, 2005, 7 (08) :1481-1484
[5]   PROBES FOR NARCOTIC RECEPTOR-MEDIATED PHENOMENA .19. SYNTHESIS OF (+)-4-[(ALPHA-R)-ALPHA-((2S,5R)-4-ALLYL-2,5-DIMETHYL-1-PIPERAZINYL)-3-METHOXYBENZYL]-N,N-DIETHYLBENZAMIDE (SNC-80) - A HIGHLY SELECTIVE, NONPEPTIDE DELTA-OPIOID RECEPTOR AGONIST [J].
CALDERON, SN ;
ROTHMAN, RB ;
PORRECA, F ;
FLIPPENANDERSON, JL ;
MCNUTT, RW ;
XU, H ;
SMITH, LE ;
BILSKY, EJ ;
DAVIS, P ;
RICE, KC .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (14) :2125-2128
[6]   Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines [J].
Cogan, DA ;
Liu, GC ;
Ellman, J .
TETRAHEDRON, 1999, 55 (29) :8883-8904
[7]  
Collman J.P., 1987, PRINCIPLES APPL ORGA
[8]   Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].
Culkin, DA ;
Hartwig, JF .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245
[9]   Concise asymmetric synthesis of α-amino acid derivatives from N-sulfinylimino esters [J].
Davis, FA ;
McCoull, W .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3396-3397
[10]   Enantioselective Rh-catalyzed arylation of N-tosylarylimines with arylboronic acids [J].
Duan, Hai-Feng ;
Jia, Yi-Xia ;
Wang, Li-Xin ;
Zhou, Qi-Lin .
ORGANIC LETTERS, 2006, 8 (12) :2567-2569