Synthesis of optically active α-aminobenzolactam via an oxidative-cyclization reaction

被引:17
作者
Chang, CY [1 ]
Yang, TK [1 ]
机构
[1] Natl Chung Hsing Univ, Dept Chem, Taichung 402, Taiwan
关键词
D O I
10.1016/S0957-4166(03)00408-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A convergent pathway for the asymmetric synthesis of (-)-alpha-aminobenzolactam I is described. For the first time, the key intermediate N-methoxybenzolactam 8 was prepared from L-homophenylalanine ethyl ester hydrochloride (LHPE.HCl) 5 by employing an oxidative cyclization in the presence of trifluoroacetic acid (TFA). (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2081 / 2085
页数:5
相关论文
共 15 条
[1]   AN EFFICIENT ASYMMETRIC-SYNTHESIS OF (R)-3-AMINO-2,3,4,5-TETRAHYDRO-1H-[1]BENZAZEPIN-2-ONE [J].
ARMSTRONG, JD ;
ENG, KK ;
KELLER, JL ;
PURICK, RM ;
HARTNER, FW ;
CHOI, WB ;
ASKIN, D ;
VOLANTE, RP .
TETRAHEDRON LETTERS, 1994, 35 (20) :3239-3242
[2]   NOTE ON THE SYNTHESIS OF AN OPTICALLY-ACTIVE ACE INHIBITOR WITH AMINO-OXO-BENZAZEPINE-1-ALKANOIC-ACID STRUCTURE BY MEANS OF AN ENANTIOCONVERGENT CRYSTALLIZATION-BASED RESOLUTION [J].
BOYER, SK ;
PFUND, RA ;
PORTMANN, RE ;
SEDELMEIER, GH ;
WETTER, HF .
HELVETICA CHIMICA ACTA, 1988, 71 (02) :337-343
[3]   A NEW OXINDOLE SYNTHESIS [J].
FLEMING, I ;
MOSES, RC ;
TERCEL, M ;
ZIV, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (03) :617-626
[4]   Oxazolidinone antibacterial agents. An enantioselective synthesis of the [6,5,5] tricyclic fused oxazolidinone ring system and application to the synthesis of a rigid DuP 721 analogue [J].
Gleave, DM ;
Brickner, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6470-6474
[5]   Novel, potent non-covalent thrombin inhibitors incorporating P3-lactam scaffolds [J].
Ho, JZ ;
Gibson, TS ;
Semple, JE .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (05) :743-748
[6]   Concise synthesis of enantiomerically pure phenylalanine, homophenylalanine, and bishomophenylalanine derivatives using organozinc chemistry: NMR studies of amino acid-derived organozinc reagents [J].
Jackson, RFW ;
Moore, RJ ;
Dexter, CS ;
Elliot, J ;
Mowbray, CE .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7875-7884
[7]   AN ELECTROPHILIC AROMATIC-SUBSTITUTION BY N-METHOXYAMIDES VIA HYPERVALENT IODINE INTERMEDIATES [J].
KIKUGAWA, Y ;
KAWASE, M .
CHEMISTRY LETTERS, 1990, (04) :581-582
[8]   AMINO ACID-DERIVED CHIRAL ACYL NITROSO-COMPOUNDS - DIASTEREOSELECTIVITY IN INTERMOLECULAR HETERO-DIELS-ALDER REACTIONS [J].
RITTER, AR ;
MILLER, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) :4602-4611
[9]   Oxidative cyclization of acyclic ureas with bis(trifluoroacetoxy)iodobenzene to generate N-substituted 2-benzimidazolinones [J].
Romero, AG ;
Darlington, WH ;
Jacobsen, EJ ;
Mickelson, JW .
TETRAHEDRON LETTERS, 1996, 37 (14) :2361-2364
[10]   Synthesis of the selective D-2 receptor agonist PNU-95666E from D-phenylalanine using a sequential oxidative cyclization strategy [J].
Romero, AG ;
Darlington, WH ;
McMillan, MW .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19) :6582-6587