Rh-catalyzed asymmetric hydrogenation of α-aryl imino esters:: An efficient enantioselective synthesis of aryl glycine derivatives

被引:115
作者
Shang, Gao [1 ]
Yang, Qin [1 ]
Zhang, Xumu [1 ]
机构
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
关键词
amino acids; asymmetric catalysis; enantioselectivity; hydrogenation; reduction;
D O I
10.1002/anie.200601540
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A highly enantioselective synthesis of aryl glycine derivatives from asymmetric hydrogenation was achieved by subjecting N-PMP-protected α-aryl imino esters to hydrogenation under Rh-bisphosphine catalysis (see scheme; PMP = para-methoxyphenyl, cod = cycloocta-1,5-diene). The PMP group could be easily removed for the preparation of enantiomerically pure aryl glycine derivatives. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6360 / 6362
页数:3
相关论文
共 34 条
[1]   Pd-catalyzed asymmetric hydrogenation of α-fluorinated iminoesters in fluorinated alcohol:: A new and catalytic enantioselective synthesis of fluoro α-amino acid derivatives [J].
Abe, H ;
Amii, H ;
Uneyama, K .
ORGANIC LETTERS, 2001, 3 (03) :313-315
[2]   Synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine derivatives: The central amino acid of vancomycin and related agents [J].
Boger, DL ;
Borzilleri, RM ;
Nukui, S .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3561-3565
[3]  
Brown J. M., 1999, COMPREHENSIVE ASYMME, V1
[4]   ENANTIOSELECTIVE HYDROGENATION OF THE C=N GROUP - A CATALYTIC ASYMMETRIC REDUCTIVE AMINATION PROCEDURE [J].
BURK, MJ ;
FEASTER, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6266-6267
[5]  
Chaloner P A., 1994, Homogeneous Hydrogenation, DOI [DOI 10.1007/978-94-017-1791-5, 10.1007/978-94-017-1791-5]
[6]   Efficient rhodium-catalyzed asymmetric hydrogenation for the synthesis of a new class of N-aryl β-amino acid derivatives [J].
Dai, Q ;
Yang, WR ;
Zhang, XM .
ORGANIC LETTERS, 2005, 7 (23) :5343-5345
[8]   RETRACTED: Asymmetric catalysis of the Strecker amino acid synthesis by a cyclic dipeptide (Retracted article. See JUN, 2023) [J].
Iyer, MS ;
Gigstad, KM ;
Namdev, ND ;
Lipton, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (20) :4910-4911
[9]   The first highly enantioselective homogeneously catalyzed asymmetric reductive amination:: Synthesis of α-N-benzylamino acids [J].
Kadyrov, R ;
Riermeier, TH ;
Dingerdissen, U ;
Tararov, V ;
Börner, A .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) :4067-4070
[10]   Catalytic enantioselective addition to imines [J].
Kobayashi, S ;
Ishitani, H .
CHEMICAL REVIEWS, 1999, 99 (05) :1069-1094