Synthesis of optically active α-aminobenzolactam via an oxidative–cyclization reaction
作者： Ching-Yao Chang , Teng-Kuei Yang
DOI: 10.1016/S0957-4166(03)00408-7
关键词: Oxidative cyclization 、 Optically active 、 Trifluoroacetic acid 、 Organic chemistry 、 Enantioselective synthesis 、 Phenylalanine 、 Growth hormone secretagogue 、 Ethyl ester 、 Hydrochloride 、 Chemistry
摘要: Abstract A convergent pathway for the asymmetric synthesis of (−)-α-aminobenzolactam 1 is described. For first time, key intermediate N-methoxybenzolactam 8 was prepared from l -homophenylalanine ethyl ester hydrochloride (LHPE·HCl) 5 by employing an oxidative cyclization in presence trifluoroacetic acid (TFA).
elsevier.com
sci-hub.se 参考文章(15)
Joseph D. Armstrong, Kan K. Eng, Jennifer L. Keller, Robert M. Purick, Frederick W. Hartner, Woo-Baeg Choi, David Askin, R.P. Volante, An efficient asymmetric synthesis of (R)-3-amino-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one Tetrahedron Letters. ,vol. 35, pp. 3239- 3242 ,(1994) , 10.1016/S0040-4039(00)76874-2
Duncan J. Wardrop, Arindrajit Basak, N-methoxy-N-acylnitrenium ions: application to the formal synthesis of (-)-TAN1251A. Organic Letters. ,vol. 3, pp. 1053- 1056 ,(2001) , 10.1021/OL015626O
Stephen K. Boyer, Rolland A. Pfund, Robert E. Portmann, Gottfried H. Sedelmeier, Hansjürg F. Wetter, Notiz zur Synthese Eines Optisch Aktiven Ace‐Hemmers mit Amino‐oxo‐benzazepin‐1‐alkansäure‐Struktur mittels enantiokonvergierender kristallisationsinduzierter Racemat‐Trennung Helvetica Chimica Acta. ,vol. 71, pp. 337- 343 ,(1988) , 10.1002/HLCA.19880710205
R. Smith, K Cheng, W. Schoen, S. Pong, G Hickey, T Jacks, B Butler, W. Chan, L. Chaung, F Judith, al. et, A nonpeptidyl growth hormone secretagogue Science. ,vol. 260, pp. 1640- 1643 ,(1993) , 10.1126/SCIENCE.8503009
Jeffrey W. H. Watthey, James L. Stanton, Mahesh Desai, Joseph E. Babiarz, Barbara M. Finn, Synthesis and biological properties of (carboxyalkyl)amino-substituted bicyclic lactam inhibitors of angiotensin converting enzyme. Journal of Medicinal Chemistry. ,vol. 28, pp. 1511- 1516 ,(1985) , 10.1021/JM00148A023
Susan Y. Tamura, Erick A. Goldman, Peter W. Bergum, J. Edward Semple, Novel benzo-fused lactam scaffolds as factor Xa inhibitors. Bioorganic & Medicinal Chemistry Letters. ,vol. 9, pp. 2573- 2578 ,(1999) , 10.1016/S0960-894X(99)00417-5
Ian Fleming, Roger C. Moses, Moana Tercel, Joseph Ziv, A new oxindole synthesis Journal of the Chemical Society, Perkin Transactions 1. pp. 617- 626 ,(1991) , 10.1039/P19910000617
Jonathan Z Ho, Tony S Gibson, J.Edward Semple, Novel, Potent Non-Covalent Thrombin Inhibitors Incorporating P3-Lactam Scaffolds Bioorganic & Medicinal Chemistry Letters. ,vol. 12, pp. 743- 748 ,(2002) , 10.1016/S0960-894X(02)00010-0
Yasuo Kikugawa, Masami Kawase, An Electrophilic Aromatic Substitution byN-MethoxyamidesviaHypervalent Iodine Intermediates Chemistry Letters. ,vol. 19, pp. 581- 582 ,(1990) , 10.1246/CL.1990.581
D. Mark Gleave, Steven J. Brickner, 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. Journal of Organic Chemistry. ,vol. 61, pp. 6470- 6474 ,(1996) , 10.1021/JO960945S