Synthesis of enantiopure allylamines by reductive alkylation of amino epoxides with organolithium reagents

被引:17
作者
Concellón, JM [1 ]
Suárez, JR [1 ]
del Solar, V [1 ]
机构
[1] Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain
关键词
D O I
10.1021/ol0529602
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Transformation of enantiopure (2R,1'S)-2-(1-aminoalkyl)epoxides 1 into the corresponding allylamines 2 is described. The opening of the epoxide ring with different organolithium compounds takes place with total selectivity and in high yields.
引用
收藏
页码:349 / 351
页数:3
相关论文
共 49 条
[11]   Synthesis of allylamines in enantiomerically pure form [J].
Concellón, JM ;
Baragaña, B ;
Riego, E .
TETRAHEDRON LETTERS, 2000, 41 (22) :4361-4362
[12]  
CRANDALL JK, 1983, ORG REACTIONS, V29, P345
[13]   BASE-PROMOTED REACTIONS OF EPOXIDES .3. CARBENOID DECOMPOSITION IN ACYCLIC DERIVATIVES [J].
CRANDALL, JK ;
LIN, LHC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (17) :4526-&
[14]  
DECHOUX L, 1996, J CHEM SOC CHEM COMM, P549
[15]  
Doris E, 1998, SYNLETT, P337
[16]  
ENDERS D, 1993, SYNLETT, P401
[17]   Enantiospecific synthesis of allylamines via the regioselective rhodium-catalyzed allylic amination reaction [J].
Evans, PA ;
Robinson, JE ;
Nelson, JD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6761-6762
[18]   Palladium/BINAP(S)-catalyzed asymmetric allylic amination [J].
Faller, JW ;
Wilt, JC .
ORGANIC LETTERS, 2005, 7 (04) :633-636
[19]  
FEHRENTZ JA, 1983, SYNTHESIS-STUTTGART, P676
[20]  
FRANCIOTTI M, 1992, SYNLETT, P137