Photochemical reaction between tertiary allylic amines and chromium carbene complexes: Synthesis of lactams via a zwitterion aza Cope rearrangement

被引:38
作者
Deur, CJ [1 ]
Miller, MW [1 ]
Hegedus, LS [1 ]
机构
[1] COLORADO STATE UNIV, DEPT CHEM, FT COLLINS, CO 80523 USA
关键词
D O I
10.1021/jo951829c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Photolysis of chromium carbene complexes in the presence of tertiary allylic amines resulted in a zwitterionic aza Cope rearrangement to produce unsaturated lactams in fair yield.
引用
收藏
页码:2871 / 2876
页数:6
相关论文
共 33 条
[1]   TRANSITION METAL-CARBENE COMPLEXES .4. ADDITION OF ISONITRILES TO METHYLMETHOXYCARBENEOPENTACARBONYL CHROMIUM [J].
AUMANN, R ;
FISCHER, EO .
CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (03) :954-&
[2]   FORMAL TOTAL SYNTHESIS OF DESERPIDINE DEMONSTRATING A VERSATILE AMINO-CLAISEN REARRANGEMENT WENKERT CYCLIZATION STRATEGY FOR THE PREPARATION OF FUNCTIONALIZED YOHIMBANE RING-SYSTEMS [J].
BAXTER, EW ;
LABAREE, D ;
AMMON, HL ;
MARIANO, PS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (21) :7682-7692
[3]   SYNTHESIS OF (-)-DELTA-N-NORMETHYLSKYTANTHINE [J].
CID, MM ;
EGGNAUER, U ;
WEBER, HP ;
POMBOVILLAR, E .
TETRAHEDRON LETTERS, 1991, 32 (49) :7233-7236
[4]   SYNTHESIS OF BETA-LACTONES BY THE PHOTOCHEMICAL-REACTIONS OF CHROMIUM ALKOXYCARBENE COMPLEXES WITH ALDEHYDES [J].
COLSON, PJ ;
HEGEDUS, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :4972-4976
[5]   STEREOCHEMICAL CONSEQUENCES OF THE LEWIS ACID-PROMOTED 3-AZA-COPE REARRANGEMENT OF N-ALKYL-N-ALLYL ENAMINES [J].
COOK, GR ;
STILLE, JR .
TETRAHEDRON, 1994, 50 (14) :4105-4124
[6]   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-&
[7]   SYNTHESIS OF OPTICALLY-ACTIVE 9-MEMBERED RING LACTAMS BY A ZWITTERIONIC, AZA-CLAISEN REACTION [J].
DIEDERICH, M ;
NUBBEMEYER, U .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (09) :1026-1028
[8]  
DOTZ KH, 1987, ORGANOMETALLICS, V6, P1424
[9]   ELECTRONIC EFFECTS ON THE STEREOCHEMICAL OUTCOME OF THE PHOTOCHEMICAL-REACTION OF CHROMIUM CARBENE COMPLEXES WITH IMINES TO FORM BETA-LACTAMS [J].
DUMAS, S ;
HEGEDUS, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :4967-4971
[10]   NEW METHODOLOGY FOR THE SYNTHESIS OF FUNCTIONALIZED INDOLIZIDINE AND QUINOLIZIDINE RING-SYSTEMS [J].
EDSTROM, ED .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (17) :6690-6692