MANIPULATION OF THE ALDOL ADDUCTS FROM LACTATE-DERIVED KETONES - A VERSATILE CHIRAL AUXILIARY FOR THE ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY CARBONYL-COMPOUNDS

被引:58
作者
PATERSON, I
WALLACE, DJ
机构
[1] University Chemical Laboratory, Cambridge, CB2 1EW, Lensfield Road
关键词
D O I
10.1016/0040-4039(94)88435-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ketones 1 and 2 can be transformed into a wide range of enantiomerically-pure anti and syn alpha-methyl-beta-hydroxy ketones and aldehydes. The alpha'-methyl group in 5 and 11 may be retained, demonstrating the use of the lactate-derived group as an optional chiral auxiliary.
引用
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页码:9087 / 9090
页数:4
相关论文
共 20 条
[1]   1,2-ANTI DIASTEREOSELECTIVE REDUCTION OF 2-ALKYL-3-HYDROXY-KETONES VIA THEIR SILYL ETHERS [J].
BLOCH, R ;
GILBERT, L ;
GIRARD, C .
TETRAHEDRON LETTERS, 1988, 29 (09) :1021-1024
[2]  
EVANS DA, 1982, TOP STEREOCHEM, V13, P1, DOI DOI 10.1002/9780470147221.CHL
[3]  
FRANKLIN AS, 1994, CONT ORGANIC SYNTHES, V1
[4]   THE RATIONAL DESIGN OF HIGHLY STEREOSELECTIVE BORON ENOLATES USING TRANSITION-STATE COMPUTER MODELING - A NOVEL, ASYMMETRIC ANTI-ALDOL REACTION FOR KETONES [J].
GENNARI, C ;
HEWKIN, CT ;
MOLINARI, F ;
BERNARDI, A ;
COMOTTI, A ;
GOODMAN, JM ;
PATERSON, I .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (19) :5173-5177
[5]  
Heathcock C. H., 1991, COMPREHENSIVE ORGANI, V2
[6]  
HEATHCOCK CH, 1984, ASYMMETRIC SYNTHESIS, V3, P111
[7]   ORGANOBORON COMPOUNDS IN ORGANIC-SYNTHESIS .4. ASYMMETRIC ALDOL REACTIONS [J].
MASAMUNE, S ;
SATO, T ;
KIM, BM ;
WOLLMANN, TA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (26) :8279-8281
[8]   LANTHANIDES IN ORGANIC-SYNTHESIS .2. REDUCTION OF ALPHA-HETEROSUBSTITUTED KETONES [J].
MOLANDER, GA ;
HAHN, G .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (07) :1135-1138
[9]   FURTHER SYNTHETIC STUDIES ON RIFAMYCIN-S [J].
NAGAOKA, H ;
KISHI, Y .
TETRAHEDRON, 1981, 37 (23) :3873-3888