The preparation of enantiomerically pure cyclopropylalanine

被引:19
作者
Boaz, NW [1 ]
Debenham, SD [1 ]
Large, SE [1 ]
Moore, MK [1 ]
机构
[1] Eastman Chem Co, Res Labs, Kingsport, TN 37662 USA
关键词
D O I
10.1016/j.tetasy.2003.07.007
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Single enantiomer cyclopropylalanine (>99.9% ee) and various derivatives were prepared using an asymmetric hydrogenation approach with a rhodium catalyst based on the methyl BoPhox(TM) ligand. N-Boc cyclopropylalanine benzyl ester was the preferred derivative, as this material is ripe for further selective reaction and can be recrystallized to >99.5%, enantiomeric excess. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3575 / 3580
页数:6
相关论文
共 31 条
[1]   Phosphinoferrocenylaminophosphines as novel and practical ligands for asymmetric catalysis [J].
Boaz, NW ;
Debenham, SD ;
Mackenzie, EB ;
Large, SE .
ORGANIC LETTERS, 2002, 4 (14) :2421-2424
[2]  
Brown J. M, 1999, COMPREHENSIVE ASYMME, VI, P121
[3]   A mild amide to carbamate transformation [J].
Burk, MJ ;
Allen, JG .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :7054-7057
[4]  
CARTER HE, 1946, ORG REACTIONS, V3, P198
[5]   INTERCEPTION AND CHARACTERIZATION OF A HYDRIDOALKYLRHODIUM INTERMEDIATE IN A HOMOGENEOUS CATALYTIC-HYDROGENATION REACTION [J].
CHAN, ASC ;
HALPERN, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (02) :838-840
[6]   IDENTIFICATION OF THE ENANTIOSELECTIVE STEP IN THE ASYMMETRIC CATALYTIC-HYDROGENATION OF A PROCHIRAL OLEFIN [J].
CHAN, ASC ;
PLUTH, JJ ;
HALPERN, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5952-5954
[7]   KINETIC RESOLUTION OF UNNATURAL AND RARELY OCCURRING AMINO-ACIDS - ENANTIOSELECTIVE HYDROLYSIS OF N-ACYL AMINO-ACIDS CATALYZED BY ACYLASE-I [J].
CHENAULT, HK ;
DAHMER, J ;
WHITESIDES, GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6354-6364
[8]  
CHRISTENSEN JV, 2001, Patent No. 0176636
[9]   THE ORIGINS OF THE ENANTIOSELECTION IN ASYMMETRIC CATALYTIC-HYDROGENATION OF AMINO-ACID PRECURSORS [J].
CHUA, PS ;
ROBERTS, NK ;
BOSNICH, B ;
OKRASINSKI, SJ ;
HALPERN, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (24) :1278-1280
[10]   A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions [J].
Corey, EJ ;
Xu, F ;
Noe, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12414-12415