ALPHA-AMINO-ACID DERIVATIVES AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS - SYNTHESIS OF SPHINGOSINE FROM ALPHA'-AMINO-ALPHA,BETA-YNONES

被引:93
作者
BOUTIN, RH [1 ]
RAPOPORT, H [1 ]
机构
[1] UNIV CALIF BERKELEY,DEPT CHEM,BERKELEY,CA 94720
关键词
D O I
10.1021/jo00376a050
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:5320 / 5327
页数:8
相关论文
共 40 条
[1]  
[Anonymous], 1959, ORGANIC REACT
[2]   ENANTIOSELECTIVE SYNTHESIS OF D-ERYTHRO-SPHINGOSINE [J].
BERNET, B ;
VASELLA, A .
TETRAHEDRON LETTERS, 1983, 24 (49) :5491-5494
[3]   THE REACTION OF LITHIUM ALUMINUM HYDRIDE WITH ALCOHOLS - LITHIUM TRI-TERT-BUTOXY-ALUMINOHYDRIDE AS A NEW SELECTIVE REDUCING AGENT [J].
BROWN, HC ;
MCFARLIN, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (20) :5372-5376
[4]   ALPHA-AMINO-ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS - AMINO ACYLATION WITH N-ACYLAMINO ACIDS [J].
BUCKLEY, TF ;
RAPOPORT, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (20) :6157-6163
[5]  
CHEREST M, 1968, TETRAHEDRON LETT, P2199
[6]   SUBSTITUTION OF 1-HALO-1-ALKYNES BY ORGANOMETALLIC DERIVATIVES OF COPPER - SYNTHESIS OF NEW CLASS OF SYNTHONS - APPLICATION TO SYNTHESIS OF BOMBYKOL [J].
COMMERCON, A ;
NORMANT, JF ;
VILLIERAS, J .
TETRAHEDRON, 1980, 36 (09) :1215-1221
[7]   ALPHA-AMINO-ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS - THE SYNTHESIS OF ALPHA'-AMINO-ALPHA, BETA-YNONES [J].
CUPPS, TL ;
BOUTIN, RH ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (21) :3972-3979
[8]   HIGHLY DIASTEREOCONTROLLED REDUCTION OF KETONES BY MEANS OF HYDROSILANES - PRACTICAL SYNTHESIS OF OPTICALLY-ACTIVE 1,2-DIOLS AND 2-AMINO ALCOHOLS OF THREO OR ERYTHRO CONFIGURATION [J].
FUJITA, M ;
HIYAMA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (16) :4629-4630
[9]   LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS [J].
GEMAL, AL ;
LUCHE, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5454-5459
[10]   REDUCTIONS OF CONJUGATED CARBONYL-COMPOUNDS WITH CYANOBOROHYDRIDE IN ACIDIC MEDIA [J].
HUTCHINS, RO ;
KANDASAMY, D .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (17) :2530-2533