SYNTHESIS OF OPTICALLY-ACTIVE 9-MEMBERED RING LACTAMS BY A ZWITTERIONIC, AZA-CLAISEN REACTION

被引:36
作者
DIEDERICH, M [1 ]
NUBBEMEYER, U [1 ]
机构
[1] FREE UNIV BERLIN,INST ORGAN CHEM,D-14195 BERLIN,GERMANY
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 09期
关键词
AZA-CLAISEN REACTION; AZONINONES; CHIRALITY TRANSFER; LACTAMS;
D O I
10.1002/anie.199510261
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Ring expansion with complete chirality transfer takes place in the title reaction in which proline derivatives 1 are converted into lactams 2 under mild conditions. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
引用
收藏
页码:1026 / 1028
页数:3
相关论文
共 34 条
[1]   STUDIES OF TRIFLUOROACETIC ACID .12. ACYL TRIFLUOROACETATES AND THEIR REACTIONS [J].
BOURNE, EJ ;
STACEY, M ;
TATLOW, JC ;
WORRALL, R .
JOURNAL OF THE CHEMICAL SOCIETY, 1954, (JUN) :2006-2012
[2]  
BRADY WT, 1976, TETRAHEDRON LETT, P1553
[3]   INTRAMOLECULAR [2+2] CYCLOADDITIONS OF KETENES TO CARBONYL GROUPS - A NOVEL SYNTHESIS OF SUBSTITUTED BENZOFURANS [J].
BRADY, WT ;
GIANG, YSF ;
MARCHAND, AP ;
WU, AH .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) :3457-3461
[4]   HALOGENATED KETENES .I. DICHLOROKETENE [J].
BRADY, WT ;
LIDDELL, HG ;
VAUGHN, WL .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (02) :626-&
[5]   ENANTIOSELECTIVE SYNTHESIS OF 3-AZABICYCLO[4.3.0]NONANE ALKALOIDS [J].
CID, MM ;
POMBOVILLAR, E .
HELVETICA CHIMICA ACTA, 1993, 76 (04) :1591-1607
[6]   SYNTHESIS OF (-)-DELTA-N-NORMETHYLSKYTANTHINE [J].
CID, MM ;
EGGNAUER, U ;
WEBER, HP ;
POMBOVILLAR, E .
TETRAHEDRON LETTERS, 1991, 32 (49) :7233-7236
[7]   ACETOACETYLATION WITH "2,2,6-TRIMETHYL-4H-1,3-DIOXIN-4-ONE - A CONVENIENT ALTERNATIVE TO DIKETENE [J].
CLEMENS, RJ ;
HYATT, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (14) :2431-2435
[8]   PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].
COREY, EJ ;
VENKATESWARLU, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+
[9]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[10]  
DIEDERICH M, 1992, THESIS BERLIN