Synthesis of N-acyl-β-aminoalcohols from N-acyloxazolidinones mediated by sodium azide

被引:6
作者
Bouzide, A [1 ]
Sauvé, G [1 ]
机构
[1] Univ Quebec, Inst Armand Frappier, INRS, Laval, PQ H7V 1B7, Canada
关键词
D O I
10.1016/S0040-4039(02)00155-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Acyl-beta-aminoalcohols were obtained efficiently via a highly endocyclic cleavage of N-acyloxazolidinones mediated by sodium azide in methanol at 40degreesC. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1961 / 1964
页数:4
相关论文
共 13 条
[1]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[2]  
Ager DJ, 1997, ALDRICHIM ACTA, V30, P3
[3]  
[Anonymous], [No title captured]
[4]   SYNTHESIS OF 5-SUBSTITUTED-3,3-DIMETHYL-2-PYRROLIDINONES - QUAT CHIRAL AUXILIARIES [J].
DAVIES, SG ;
DOISNEAU, GJM ;
PRODGER, JC ;
SANGANEE, HJ .
TETRAHEDRON LETTERS, 1994, 35 (15) :2369-2372
[5]   Identification of MK-944a: A second clinical candidate from the hydroxylaminepentanamide isostere series of HIV protease inhibitors [J].
Dorsey, BD ;
McDonough, C ;
McDaniel, SL ;
Levin, RB ;
Newton, CL ;
Hoffman, JM ;
Darke, PL ;
Zugay-Murphy, JA ;
Emini, EA ;
Schleif, WA ;
Olsen, DB ;
Stahlhut, MW ;
Rutkowski, CA ;
Kuo, LC ;
Lin, JH ;
Chen, IW ;
Michelson, SR ;
Holloway, MK ;
Huff, JR ;
Vacca, JP .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (18) :3386-3399
[6]   CONTRASTERIC CARBOXIMIDE HYDROLYSIS WITH LITHIUM HYDROPEROXIDE [J].
EVANS, DA ;
BRITTON, TC ;
ELLMAN, JA .
TETRAHEDRON LETTERS, 1987, 28 (49) :6141-6144
[7]   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
[8]   Mild and selective sodium azide mediated cleavage of p-nitrobenzoic esters [J].
Gómez-Vidal, JA ;
Forrester, MT ;
Silverman, RB .
ORGANIC LETTERS, 2001, 3 (16) :2477-2479
[9]   Total synthesis of myxalamide A [J].
Mapp, AK ;
Heathcock, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :23-27
[10]   Comparative binding energy analysis of HIV-1 protease inhibitors:: Incorporation of solvent effects and validation as a powerful tool in receptor-based drug design [J].
Pérez, C ;
Pastor, M ;
Ortiz, AR ;
Gago, F .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (06) :836-852