A simple, high yield route to cis-4-(N-alkylamino)-L-prolines

被引:4
作者
Curran, TP [1 ]
Marques, KA
Bilimoria, SI
机构
[1] Trinity Coll, Dept Chem, Hartford, CT 06106 USA
[2] Coll Holy Cross, Dept Chem, Worcester, MA 01610 USA
关键词
aminoproline; reductive amination; azide; aldehyde; secondary amine;
D O I
10.2174/1570178053400063
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of 1 equivalent of N-alpha-acetyl-cis-4-azido-L-proline with I equivalent of an aldehyde and a catalytic amount of Pd-C under an H-2 atmosphere cleanly and efficiently yields the corresponding N-alpha-acetyl-cis-4-(N-gamma-alkylamino)-L-proline derivative.
引用
收藏
页码:15 / 17
页数:3
相关论文
共 23 条
[1]   DESIGN, SYNTHESIS, AND TESTING OF ANTISICKLING AGENTS .2. PROLINE DERIVATIVES DESIGNED FOR THE DONOR SITE [J].
ABRAHAM, DJ ;
MOKOTOFF, M ;
SHEH, L ;
SIMMONS, JE .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (04) :549-554
[2]   Enhanced triple helix stability of collagen peptides with 4R-aminoprolyl (Amp) residues:: Relative roles of electrostatic and hydrogen bonding effects [J].
Babu, IR ;
Ganesh, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (09) :2079-2080
[3]   4-SUBSTITUTED PROLINE DERIVATIVES THAT INHIBIT ANGIOTENSIN-CONVERTING ENZYME AND NEUTRAL ENDOPEPTIDASE-24.11 [J].
BHAGWAT, SS ;
FINK, CA ;
GUDE, C ;
CHAN, K ;
QIAO, Y ;
SAKANE, Y ;
BERRY, C ;
GHAI, RD .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (22) :2673-2676
[4]   N-alpha-benzoyl-cis-4-amino-L-proline: A gamma-turn mimetic [J].
Curran, TP ;
Chandler, NM ;
Kennedy, RJ ;
Keaney, MT .
TETRAHEDRON LETTERS, 1996, 37 (12) :1933-1936
[5]   Chiral analogues of peptide nucleic acids: Synthesis of 4-aminoprolyl nucleic acids and DNA complementation studies using UV/CD spectroscopy [J].
Gangamani, BP ;
Kumar, VA ;
Ganesh, KN .
TETRAHEDRON, 1999, 55 (01) :177-192
[6]   Short, highly efficient syntheses of protected 3-azido- and 4-azidoproline and their precursors [J].
Gómez-Vidal, JA ;
Silverman, RB .
ORGANIC LETTERS, 2001, 3 (16) :2481-2484
[7]   PALLADIUM-MEDIATED STEREOCONTROLLED REDUCTIVE AMINATION OF AZIDO SUGARS PREPARED FROM ENZYMATIC ALDOL CONDENSATION - A GENERAL-APPROACH TO THE SYNTHESIS OF DEOXY AZA SUGARS [J].
KAJIMOTO, T ;
CHEN, LR ;
LIU, KKC ;
WONG, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (17) :6678-6680
[8]   Total synthesis and antifungal evaluation of cyclic aminohexapeptides [J].
Klein, LL ;
Li, LP ;
Chen, HJ ;
Curty, CB ;
DeGoey, DA ;
Grampovnik, DJ ;
Leone, CL ;
Thomas, SA ;
Yeung, CM ;
Funk, KW ;
Kishore, V ;
Lundell, EO ;
Wodka, D ;
Meulbroek, JA ;
Alder, JD ;
Nilius, AM ;
Lartey, PA ;
Plattner, JJ .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (07) :1677-1696
[9]   ANALOGS AND HOMOLOGS OF PROLINE AND HYDROXYPROLINE [J].
MAUGER, AB ;
WITKOP, B .
CHEMICAL REVIEWS, 1966, 66 (01) :47-+
[10]   Enantiospecific syntheses of (R)- and (S)-proline and some derivatives from D-glucono-1,5-lactone [J].
Mazzini, C ;
Sambri, L ;
Regeling, H ;
Zwanenburg, B ;
Chittenden, GJF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (22) :3351-3356