Vanadium-catalyzed anti-selective additions of allenols to imines

被引:45
作者
Trost, BM [1 ]
Jonasson, C [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
关键词
allenols; asymmetric catalysis; atom economy; imines; sigmatropic rearrangement; vanadium;
D O I
10.1002/anie.200350890
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An atom-economic route to versatile building blocks: Vanadium enolates, which were generated in situ by the [3,3] sigmatropic rearrangement of vanadyl esters of allenic alcohols, undergo facile addition to imines derived from aromatic aldehydes to yield bifunctional β′-aminoα,β-unsaturated enones [Eq. (1)]. With 1,3-disubstituted allenes, good anti selectivity is observed in most cases.
引用
收藏
页码:2063 / 2066
页数:4
相关论文
共 27 条
[1]  
Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
[2]  
2-E
[3]  
Arend M., 1998, ANGEW CHEM, V110, P1096, DOI DOI 10.1002/(SICI)1521-3757(19980420)110:8
[4]  
ARNOLD DI, 2001, TETRAHEDRON, V57, P771
[5]   USE OF OXO-METALLIC DERIVATIVES IN ISOMERIZATION-REACTIONS OF UNSATURATED ALCOHOLS [J].
CHABARDES, P ;
KUNTZ, E ;
VARAGNAT, J .
TETRAHEDRON, 1977, 33 (14) :1775-1783
[6]   ALLENES .24. PREPARATION OF ALPHA-ALLENIC ALCOHOLS FROM MONO-O-TETRAHYDROPYRAN-2-YL DERIVATIVES OF BUTYNE-1,4-DIOLS [J].
COWIE, JS ;
LANDOR, PD ;
LANDOR, SR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (07) :720-724
[7]  
DENMARK SE, COMPREHENSIVE ASYMME, P954
[8]  
Enders D, 2000, SYNLETT, P644
[9]  
ERMAN MB, 1976, TETRAHEDRON LETT, P2981
[10]   PREPARATION OF PRIMARY AMINES AND 2-AZETIDINONES VIA N-TRIMETHYLSILYL IMINES [J].
HART, DJ ;
KANAI, K ;
THOMAS, DG ;
YANG, TK .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (03) :289-294