Highly diastereoselective synthesis of new optically active aminoalcohols in one step from (+)-camphor and (-)-fenchone

被引:89
作者
Genov, M [1 ]
Kostova, K [1 ]
Dimitrov, V [1 ]
机构
[1] BULGARIAN ACAD SCI,INST ORGAN CHEM,BG-1113 SOFIA,BULGARIA
关键词
D O I
10.1016/S0957-4166(97)00182-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
New optically active aminoalcohols have been prepared from CeCl3-activated (+)-camphor and (-)-fenchone and N-functionalized organolithium compounds. The aminoalcohols obtained catalyze the addition of diethylzinc to benzaldehyde in high yields and enantioselectivities up to 64%. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:1869 / 1876
页数:8
相关论文
共 23 条
[1]   THE CHIRAL POOL AS A SOURCE OF ENANTIOSELECTIVE CATALYSTS AND AUXILIARIES [J].
BLASER, HU .
CHEMICAL REVIEWS, 1992, 92 (05) :935-952
[2]  
BRANDSMA L, 1987, PREPARATIVE POLAR OR, V1, P114
[3]   HIGH-YIELD SYNTHESES OF DILITHIO-DERIVATIVES OF FURAN, THIOPHENE, N-METHYLPYRROLE, 3-METHYLFURAN, AND 3-METHYLTHIOPHEN - APPLICATION OF METHOD TO 2-METHYLFURAN, 2-METHYLTHIOPHEN, 2,5-DIMETHYLFURAN, 2,5-DIMETHYLTHIOPHEN, BENZO[B]FURAN, BENZO[B]THIOPHEN, PYRROLE, AND INDOLE [J].
CHADWICK, DJ ;
WILLBE, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (08) :887-893
[4]   DIASTEREOISOMERIC PURE 2-(1-HYDROXYALKYL)PYRIDINES AS CATALYSTS IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES [J].
CHELUCCI, G ;
SOCCOLINI, F .
TETRAHEDRON-ASYMMETRY, 1992, 3 (10) :1235-1238
[5]   CERIUM(III) CHLORIDE AS CATALYTIC AND STOICHIOMETRIC PROMOTER OF THE QUANTITATIVE ADDITION OF ORGANOMETALLIC REAGENTS TO (+)-CAMPHOR AND (-)-FENCHONE [J].
DIMITROV, V ;
BRATOVANOV, S ;
SIMOVA, S ;
KOSTOVA, K .
TETRAHEDRON LETTERS, 1994, 35 (36) :6713-6716
[6]   Synthesis and absolute configuration of new chiral epoxyalcohols by stereoselective epoxidation of allylic and homoallylic alcohols with a (1R)-(+)-camphor skeleton [J].
Dimitrov, V ;
Philipova, I ;
Simova, S .
TETRAHEDRON-ASYMMETRY, 1996, 7 (05) :1493-1500
[7]   Highly effective and practical stereoselective synthesis of new homoallylic alcohols with (+)-camphor and (-)-fenchone skeleton [J].
Dimitrov, V ;
Simova, S ;
Kostova, K .
TETRAHEDRON, 1996, 52 (05) :1699-1706
[8]   SYNTHESIS OF NEW OPTICALLY-ACTIVE 1,3-DIOLS WITH CAMPHOR AND FENCHONE SKELETON [J].
DIMITROV, V ;
KOSTOVA, K ;
HESSE, M .
TETRAHEDRON-ASYMMETRY, 1994, 5 (10) :1891-1894
[9]   Anhydrous cerium(III) chloride - Effect of the drying process on activity and efficiency [J].
Dimitrov, V ;
Kostova, K ;
Genov, M .
TETRAHEDRON LETTERS, 1996, 37 (37) :6787-6790
[10]   Cerium(III) chloride mediated addition of mono- and dilithium ferrocene to (+)-camphor and (-)-fenchone: Synthesis and structure of new chiral ferrocenyl alcohols and diols [J].
Dimitrov, V ;
Genov, M ;
Simova, S ;
Linden, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 525 (1-2) :213-224