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
[11]  
HAN YL, 1989, TETRAHEDRON LETT, V30, P528
[12]   UBER ALKYLENIMIN-DERIVATE .12. PIPERIDIN-DERIVATE MIT ZENTRALERREGENDER WIRKUNG-II [J].
HEER, J ;
SURY, E ;
HOFFMANN, K .
HELVETICA CHIMICA ACTA, 1955, 38 (01) :134-140
[13]   Concerning the derivatives of the alpha-amino-n-butyric acid. [J].
Hildesheimer, A .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1910, 43 :2796-2805
[14]   AMIDOACETONE ENOLATE ANIONS - ALKYLATION AND MICHAEL REACTION [J].
HOYE, TR ;
DUFF, SR ;
KING, RS .
TETRAHEDRON LETTERS, 1985, 26 (29) :3433-3436
[15]   CATALYTIC-HYDROGENATION OF PYRROLES AT ATMOSPHERIC-PRESSURE [J].
KAISER, HP ;
MUCHOWSKI, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (22) :4203-4209
[16]   ALPHA-AMINO-ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS - AMINOACYLATION OF METALLO ALKYLS AND ALKENYLS [J].
KNUDSEN, CG ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (13) :2260-2266
[17]  
KRAPCHO AP, 1976, TETRAHEDRON LETT, P2205
[18]   ALPHA-AMINO-ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS - ALKYLATION OF N-PHENYLFLUORENYL ALPHA-AMINO KETONES - SYNTHESIS OF OPTICALLY PURE ALPHA-ALKYL CARBOXYLIC-ACIDS [J].
LUBELL, WD ;
RAPOPORT, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) :7447-7455
[19]   NEW TRIALKYLSILYL ENOL ETHER CHEMISTRY - REGIOSPECIFIC AND STEREOSPECIFIC SEQUENTIAL ELECTROPHILIC ADDITION [J].
MAGNUS, P ;
MUGRAGE, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (01) :462-464
[20]   ALPHA-AMINO-ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS - A GENERAL-SYNTHESIS OF D-ALPHA-AMINO ACIDS FROM L-SERINE [J].
MAURER, PJ ;
TAKAHATA, H ;
RAPOPORT, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (04) :1095-1098