Steroidal ureas as enantioselective receptors for an N-acetyl α-amino carboxylate

被引:49
作者
Siracusa, L
Hurley, FM
Dresen, S
Lawless, LJ
Pérez-Payán, MN
Davis, AP
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
[2] Univ Dublin Trinity Coll, Dept Chem, Dublin 2, Ireland
关键词
D O I
10.1021/ol027009l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cholic acid has been elaborated into three regioisomeric bis-carbamoylureas, which have been investigated as enantioselective receptors for N-acetyl phenylalanine. L/D selectivities, peaking at 5:1, have been determined by a sensitive and rapid MS-based extraction method that should be generalizable to related systems.
引用
收藏
页码:4639 / 4642
页数:4
相关论文
共 32 条
[21]   Steroidal guanidines as enantioselective receptors for N-acyl α-amino acids.: Part 1.: 3α-Guanylated carbamates derived from cholic acid [J].
Lawless, LJ ;
Blackburn, AG ;
Ayling, AJ ;
Pérez-Payán, MN ;
Davis, AP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (11) :1329-1341
[22]   Efficient recognition of chiral carbamoyl-alpha-hydroxyacids with a cleft-type receptor [J].
Martin, M ;
Raposo, C ;
Almaraz, M ;
Crego, M ;
Caballero, C ;
Grande, M ;
Moran, JR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (20) :2386-2388
[23]   Multifunctional and chiral porphyrins: Model receptors for chiral recognition [J].
Ogoshi, H ;
Mizutani, T .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (02) :81-89
[24]   HOST-GUEST COMPLEXATION .13. HIGH CHIRAL RECOGNITION OF AMINO ESTERS BY DILOCULAR HOSTS CONTAINING EXTENDED STERIC BARRIERS [J].
PEACOCK, SC ;
DOMEIER, LA ;
GAETA, FCA ;
HELGESON, RC ;
TIMKO, JM ;
CRAM, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (26) :8190-8202
[25]   Intermolecular H-1-H-1 two dimensional nuclear overhauser enhancements in the characterization of a rationally designed chiral recognition system [J].
Pirkle, WH ;
Murray, PG ;
Rausch, DJ ;
McKenna, ST .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4769-4774
[26]  
Reetz MT, 1999, ANGEW CHEM INT EDIT, V38, P1758, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1758::AID-ANIE1758>3.0.CO
[27]  
2-8
[28]   ENANTIOSELECTIVE AND DIASTEREOSELECTIVE MOLECULAR RECOGNITION OF NEUTRAL MOLECULES [J].
WEBB, TH ;
WILCOX, CS .
CHEMICAL SOCIETY REVIEWS, 1993, 22 (06) :383-395
[29]   Enantioselective resolving resins from a combinatorial library. Kinetic resolution of cyclic amino acid derivatives [J].
Weingarten, MD ;
Sekanina, K ;
Still, WC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) :9112-9113
[30]   Improved method for rapid evaluation of chiral stationary phase libraries [J].
Welch, CJ ;
Pollard, SD ;
Mathre, DJ ;
Reider, PJ .
ORGANIC LETTERS, 2001, 3 (01) :95-98