ALKYLATION OF ALPHA-TERT-BUTOXYCARBONYLAMINO KETONE ENOLATE ANIONS - A USEFUL SYNTHESIS OF ALPHA-ALKYL-ALPHA-AMINO KETONES, 2-ACYLPYRROLIDINES, AND 2-ACYLPIPERIDINES

被引:11
作者
GUZMAN, A
QUINTFRO, C
MUCHOWSKI, JM
机构
[1] SYNTEX INC,RES,INST ORGAN CHEM,3401 HILLVIEW AVE,PALO ALTO,CA 94304
[2] SYNTEX SA CV,DIV INVEST,MEXICO CITY 10,DF,MEXICO
来源
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1991年 / 69卷 / 12期
关键词
ALPHA-TERT-BUTOXYCARBONYLAMINO KETONES; ALPHA-ALKYL-ALPHA-AMINO KETONES; 2-ACYLPYRROLIDINES; AND; 2-ACYLPIPERIDINES;
D O I
10.1139/v91-298
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A versatile synthesis of alpha-alkyl-alpha-amino ketones 5 and cyclic alpha-amino ketones 7 based on the selective mono-alpha-alkylation and C(alpha), N-cycloalkylation of alpha-tert-butoxycarbonylamino ketones 2 and subsequent acidic hydrolysis is described.
引用
收藏
页码:2059 / 2063
页数:5
相关论文
共 27 条
[1]   ALKYLATION OF ALPHA-FORMAMIDO KETONE ENOLATE ANIONS - A VERSATILE SYNTHESIS OF ALPHA-ALKYL ALPHA-AMINO KETONES [J].
ACKRELL, J ;
MUCHOWSKI, JM ;
GALEAZZI, E ;
GUZMAN, A .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (17) :3374-3376
[2]   DIPOLE-STABILIZED CARBANIONS - NOVEL AND USEFUL INTERMEDIATES [J].
BEAK, P ;
REITZ, DB .
CHEMICAL REVIEWS, 1978, 78 (03) :275-316
[3]   NITROGEN ACIDS .1. CARBOXAMIDES AND SULFONAMIDES [J].
BORDWELL, FG ;
ALGRIM, D .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (14) :2507-2508
[4]  
BRINGMANN G, 1989, SYNTHESIS-STUTTGART, P608
[5]   ALPHA-AMINO-ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS - AMINO ACYLATION WITH N-ACYLAMINO ACIDS [J].
BUCKLEY, TF ;
RAPOPORT, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (20) :6157-6163
[6]   STEREOSELECTIVE APPROACHES TO TRISUBSTITUTED PYRROLIDINES [J].
BURNS, B ;
COATES, B ;
NEESON, S ;
STEVENSON, PJ .
TETRAHEDRON LETTERS, 1990, 31 (30) :4351-4354
[7]   ALPHA-AMINO-ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS - THE SYNTHESIS OF ALPHA'-AMINO-ALPHA, BETA-YNONES [J].
CUPPS, TL ;
BOUTIN, RH ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (21) :3972-3979
[8]   SYNTHESIS AND REDUCTION OF ALPHA-AMINO KETONES DERIVED FROM LEUCINE [J].
DUFOUR, MN ;
JOUIN, P ;
PONCET, J ;
PANTALONI, A ;
CASTRO, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (11) :1895-1899
[9]   SYNTHESIS OF ALPHA-AMINOALDEHYDES AND ALPHA-AMINOKETONES - A REVIEW [J].
FISHER, LE ;
MUCHOWSKI, JM .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1990, 22 (04) :399-484
[10]  
HAN YL, 1990, SYNTHESIS-STUTTGART, P122