Diastereo- and enantioselective Diels-Alder reactions of 2-amino-1,3-dienes

被引:63
作者
Enders, D
Meyer, O
机构
[1] Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, D-52074 Aachen
来源
LIEBIGS ANNALEN | 1996年 / 07期
关键词
2-amino-1,3-dienes; enamines; cross conjugated; 4 + 2] cycloadditions; nitrocyclohexanones; 4-piperidinones; cycloheptandione derivatives; Danishefsky dienes;
D O I
10.1002/jlac.199619960702
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The employment of 2-amino substituted 1,3-dienes in cycloaddition reactions has recently extended the scope of Diels-Alder methodologies. In this review, the preparation of a variety of 2-amino-1,3-dienes is presented, and the use of these cross conjugated enamines in normal as well as hetero Diels-Alder reactions is depicted. Diastereo- and enantioselective variations show new aspects for the preparation of cyclic carbonyl compounds in a highly stereoselective fashion. Further cyclisation reactions e.g. cyclopropanation reactions are also considered in this account.
引用
收藏
页码:1023 / 1035
页数:13
相关论文
共 86 条
[1]  
[Anonymous], ORGANIC SYNTHESIS HI
[2]  
ARNOLD Z, 1990, SYNTHESIS-STUTTGART, P39
[3]   2-MORPHOLINOBUTADIENES AS SYNTHON FOR THE REGIOSELECTIVE PREPARATION OF 3-MORPHOLINO-1,4-PENTADIENES AND BETA-HYDROXYVINYLKETONES [J].
BARLUENGA, J ;
AZNAR, F ;
CABAL, MP ;
VALDES, C .
TETRAHEDRON LETTERS, 1989, 30 (43) :5923-5926
[4]   REACTIVITY OF 2-MORPHOLINOBUTADIENES WITH HETEROCUMULENES - STEREOSELECTIVE SYNTHESIS OF THIINS AND NEW 2-MORPHOLINOBUTADIENE DERIVATIVES [J].
BARLUENGA, J ;
AZNAR, F ;
VALDES, C ;
ORTIZ, FL .
TETRAHEDRON LETTERS, 1990, 31 (36) :5237-5240
[5]   ANNULATION REACTION OF VINYLALMINOCARBENES - CHARACTERIZATION OF THE TETRACARBONYL VINYLCARBENE AND METALAHEXATRIENE INTERMEDIATES [J].
BARLUENGA, J ;
AZNAR, F ;
MARTIN, A ;
GARCIAGRANDA, S ;
PEREZCARRENO, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) :11191-11192
[6]  
BARLUENGA J, 1984, SYNTHESIS-STUTTGART, P304
[7]   A SIMPLE AND EFFICIENT SYNTHESIS OF 2-AMINO-1,3-BUTADIENES FROM BETA-ENAMINO PHOSPHONIUM SALTS [J].
BARLUENGA, J ;
MERINO, I ;
PALACIOS, F .
TETRAHEDRON LETTERS, 1990, 31 (46) :6713-6716
[8]   ALKYNYLMERCURY CHLORIDE OR ACETATE AS INTERMEDIATES IN THE MERCURY(II) SALT-PROMOTED ADDITION OF ALIPHATIC AND AROMATIC-AMINES TO TERMINAL ACETYLENES [J].
BARLUENGA, J ;
AZNAR, F ;
LIZ, R ;
RODES, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (05) :1087-1091
[9]   SYNTHESIS OF 1-AZA-1,3-DIENES AND 2-MORPHOLINO-1,3-DIENES VIA CATALYTIC AMINOMERCURIATION OF ALK-3-EN-1-YNES [J].
BARLUENGA, J ;
AZNAR, F ;
LIZ, R ;
CABAL, MP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (20) :1375-1376
[10]  
BARLUENGA J, 1986, SYNTHESIS-STUTTGART, P960