ASYMMETRIC CONJUGATE ADDITION;
MANNICH-TYPE REACTIONS;
DIRECT ALDOL REACTION;
STEREOSELECTIVE-SYNTHESIS;
1,3-DICARBONYL COMPOUNDS;
POLYKETIDE SYNTHASES;
NITROALDOL REACTION;
BOND FORMATION;
KETO ESTERS;
NITROOLEFINS;
D O I:
10.1021/ol102289g
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
The first organocatalytic enantio- and diastereoselective conjugate addition of alpha-ketoamides to nitroalkenes has been achieved using a bifunctional amino thiourea catalyst. In this new approach, the substrate amide proton plays a critical role in the formation of the Michael anti-adducts in high yields and high stereoselectivities. To illustrate the high synthetic potential of this methodology, the diastereo- and enantioselective synthesis of a hexasubstituted cyclohexane via a Michael-Michael-Henry cascade reaction is described.
机构:
Aix Marseille Univ, CNRS, UMR 6263, iSm2,Ctr St Jerome, F-13397 Marseille, FranceAix Marseille Univ, CNRS, UMR 6263, iSm2,Ctr St Jerome, F-13397 Marseille, France
Allais, Christophe
Constantieux, Thierry
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h-index: 0
机构:
Aix Marseille Univ, CNRS, UMR 6263, iSm2,Ctr St Jerome, F-13397 Marseille, FranceAix Marseille Univ, CNRS, UMR 6263, iSm2,Ctr St Jerome, F-13397 Marseille, France
Constantieux, Thierry
Rodriguez, Jean
论文数: 0引用数: 0
h-index: 0
机构:
Aix Marseille Univ, CNRS, UMR 6263, iSm2,Ctr St Jerome, F-13397 Marseille, FranceAix Marseille Univ, CNRS, UMR 6263, iSm2,Ctr St Jerome, F-13397 Marseille, France
机构:
Aix Marseille Univ, CNRS, UMR 6263, iSm2,Ctr St Jerome, F-13397 Marseille, FranceAix Marseille Univ, CNRS, UMR 6263, iSm2,Ctr St Jerome, F-13397 Marseille, France
Allais, Christophe
Constantieux, Thierry
论文数: 0引用数: 0
h-index: 0
机构:
Aix Marseille Univ, CNRS, UMR 6263, iSm2,Ctr St Jerome, F-13397 Marseille, FranceAix Marseille Univ, CNRS, UMR 6263, iSm2,Ctr St Jerome, F-13397 Marseille, France
Constantieux, Thierry
Rodriguez, Jean
论文数: 0引用数: 0
h-index: 0
机构:
Aix Marseille Univ, CNRS, UMR 6263, iSm2,Ctr St Jerome, F-13397 Marseille, FranceAix Marseille Univ, CNRS, UMR 6263, iSm2,Ctr St Jerome, F-13397 Marseille, France