Synthesis of benzylcyanoborane adducts of amines and separation of their enantiomers;: SN2 substitution at boron atom

被引:25
作者
Charoy, L
Valleix, A
Toupet, L
Le Gall, T
van Chuong, PP
Mioskowski, C
机构
[1] CEA Saclay, Serv Mol Marquees, Dept Biol Cellulaire & Mol, F-91191 Gif Sur Yvette, France
[2] Univ Rennes 1, Grp Mat Condense & Mat, UMR 6626, F-35042 Rennes, France
关键词
D O I
10.1039/b006265k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Benzylcyanoborane adducts of several amines were prepared in four steps from toluene, their enantiomers were separated using chiral phase HPLC and an S(N)2 pathway was evidenced in the reaction of a trimethylamine-derived enantiomer with pyridine.
引用
收藏
页码:2275 / 2276
页数:2
相关论文
共 26 条
[1]  
[Anonymous], MAIN GROUP METAL CHE
[2]   Resolution of alpha-aminoboronic esters by diastereoselective crystallization with pinanediols. Confirmation by x-ray analysis [J].
Brosz, CS ;
Calabrese, JC ;
Kettner, CA ;
Teleha, CA .
TETRAHEDRON-ASYMMETRY, 1997, 8 (09) :1435-1440
[3]   ORGANOBORANES .48. IMPROVED PROCEDURES FOR THE PREPARATION OF BORONIC AND BORINIC ESTERS [J].
BROWN, HC ;
SREBNIK, M ;
COLE, TE .
ORGANOMETALLICS, 1986, 5 (11) :2300-2303
[4]   A NEW METHOD FOR THE SYNTHESIS OF CYANOHYDROBORATES AND CYANOBORANE COMPLEXES [J].
EMRI, J ;
GYORI, B .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (22) :1303-1304
[5]   An enantiomerically pure tetracoordinate boron compound: Stereochemistry of substitution reactions at the chirogenic boron atom [J].
Imamoto, T ;
Morishita, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (26) :6329-6330
[6]   THE EFFICIENT SYNTHESIS AND SIMPLE RESOLUTION OF A PROLINEBORONATE ESTER SUITABLE FOR ENZYME-INHIBITION STUDIES [J].
KELLY, TA ;
FUCHS, VU ;
PERRY, CW ;
SNOW, RJ .
TETRAHEDRON, 1993, 49 (05) :1009-1016
[7]  
KETTNER CA, 1984, J BIOL CHEM, V259, P5106
[8]  
Lebarbier C, 1996, SYNTHESIS-STUTTGART, P1371
[9]   New asymmetric synthesis of alpha-aminoboronic acids containing functionalized side chains [J].
Mantri, P ;
Duffy, DE ;
Kettner, CA .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5690-5692
[10]   (R)-1-ACETAMIDO-2-PHENYLETHANEBORONIC ACID - A SPECIFIC TRANSITION-STATE ANALOG FOR CHYMOTRYPSIN [J].
MATTESON, DS ;
SADHU, KM ;
LIENHARD, GE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (17) :5241-5242