Catalytic enantioselective alkylation of benzaldehyde with diethylzinc using chiral nonracemic (thio)-phosphoramidates

被引:36
作者
Hulst, R [1 ]
Heres, H [1 ]
Fitzpatrick, K [1 ]
Peper, NCMW [1 ]
Kellogg, RM [1 ]
机构
[1] UNIV GRONINGEN,GRONINGEN CTR CATALYSIS & SYNTH,DEPT ORGAN & MOL INORGAN CHEM,NL-9747 AG GRONINGEN,NETHERLANDS
关键词
D O I
10.1016/0957-4166(96)00355-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Two chiral nonracemic gamma-amino alcohols, ephedrine thiol and the corresponding (thio)-phosphoramidates have been examined as catalysts for the enantioselective alkylation of benzaldehyde by diethylzinc. Addition of titanium tetraisopropoxide increases the yield as well as the enantioselectivity; 1-phenyl-propanol is obtained in up to 98% yield and e.e. Copyright (C) 1996 Published by Elsevier Science Ltd
引用
收藏
页码:2755 / 2760
页数:6
相关论文
共 28 条
[1]   ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO BENZALDEHYDE IN THE PRESENCE OF EPHEDRINE DERIVATIVES [J].
CHALONER, PA ;
PERERA, SAR .
TETRAHEDRON LETTERS, 1987, 28 (26) :3013-3014
[2]   CATALYTIC ASYMMETRIC PREPARATION OF POLYFUNCTIONAL PROTECTED 1,2-DIOLS AND EPOXIDES [J].
EISENBERG, C ;
KNOCHEL, P .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (14) :3760-3761
[3]   THIOL AND DISULFIDE DERIVATIVES OF EPHEDRA ALKALOIDS .2. A MECHANISTIC STUDY OF THEIR EFFECT ON THE ADDITION OF DIETHYL ZINC TO BENZALDEHYDE [J].
FITZPATRICK, K ;
HULST, R ;
KELLOGG, RM .
TETRAHEDRON-ASYMMETRY, 1995, 6 (08) :1861-1864
[4]   SULFUR DERIVATIVES OF EPHEDRA ALKALOIDS - NEW AND HIGHLY EFFICIENT CHIRAL CATALYSTS [J].
HOF, RP ;
POELERT, MA ;
PEPER, NCMW ;
KELLOGG, RM .
TETRAHEDRON-ASYMMETRY, 1994, 5 (01) :31-34
[5]  
HULST R, 1995, RECL TRAV CHIM PAY B, V114, P115
[6]   ALPHA-PHENYLETHYLAMINE BASED CHIRAL PHOSPHOLIDINES - NEW AGENTS FOR THE DETERMINATION OF THE ENANTIOMERIC EXCESS OF CHIRAL ALCOHOLS, AMINES AND THIOLS BY MEANS OF P-31 NMR [J].
HULST, R ;
DEVRIES, NK ;
FERINGA, BL .
TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :699-708
[7]  
HULST R, 1996, TETRAHEDRON-ASYMMETR, V5, P1373
[8]  
ITO K, 1992, SYNLETT, P573
[9]  
KANG J, 1994, SYNLETT, P842
[10]   ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALPHA-BRANCHED ALDEHYDES [J].
KANG, J ;
LEE, JW ;
KIM, JI .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (17) :2009-2010