Efficient asymmetric synthesis of α-trifluoromethyl-substituted primary amines via nucleophilic 1,2-addition to trifluoroacetaldehyde SAMP- or RAMP-hydrazone

被引:68
作者
Enders, D [1 ]
Funabiki, K [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
关键词
D O I
10.1021/ol015869g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] An efficient asymmetric synthesis of alpha -trifluoromethyl-substituted primary amines via nucleophilic 1,2-addition of alkyllithium reagents to trifluoroacetaldehyde SAMP- or RAMP-hydrazone followed by benzoylation and SmI2-promoted nitrogen-nitrogen single bond cleavage is described.
引用
收藏
页码:1575 / 1577
页数:3
相关论文
共 44 条
[1]   AMINATION WITH 3-ACETOXYAMINOQUINAZOLIN-4-(3H)ONES - PREPARATION OF ALPHA-AMINO-ACID ESTERS BY REACTION WITH SILYL KETENE ACETALS FOLLOWED BY N-N BOND-CLEAVAGE [J].
ATKINSON, RS ;
KELLY, BJ ;
WILLIAMS, J .
TETRAHEDRON, 1992, 48 (36) :7713-7730
[2]   CONVENIENT GENERAL-METHOD FOR THE PREPARATION OF PRIMARY ALKYLLITHIUMS BY LITHIUM IODINE EXCHANGE [J].
BAILEY, WF ;
PUNZALAN, ER .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) :5404-5406
[3]   Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].
Bloch, R .
CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438
[4]  
BRAVO P, 1999, ASYMMETRIC FLUOROORG, P98
[5]  
BRAVO P, 1999, ENANTIOCONTROLLED SY, P107
[6]   ENANTIOSELECTIVE HYDROGENATION OF THE C=N GROUP - A CATALYTIC ASYMMETRIC REDUCTIVE AMINATION PROCEDURE [J].
BURK, MJ ;
FEASTER, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6266-6267
[7]   CATALYTIC ASYMMETRIC REDUCTIVE AMINATION OF KETONES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION OF THE C=N DOUBLE-BOND [J].
BURK, MJ ;
MARTINEZ, JP ;
FEASTER, JE ;
COSFORD, N .
TETRAHEDRON, 1994, 50 (15) :4399-4428
[8]  
Denmark S. E., 1996, J CHEM SOC CHEM COMM, P999
[9]   Asymmetric synthesis of amines by nucleophilic 1,2-addition of organometallic reagents to the CN-double bond [J].
Enders, D ;
Reinhold, U .
TETRAHEDRON-ASYMMETRY, 1997, 8 (12) :1895-1946
[10]  
Enders D., 1984, ASYMMETRIC SYNTHES B, V3, P275