STEREODIVERGENT SYNTHESIS OF FLUORINATED THREONINE DERIVATIVES IN HIGH OPTICAL PURITY

被引:22
作者
SHIMIZU, M [1 ]
YOKOTA, T [1 ]
FUJIMORI, K [1 ]
FUJISAWA, T [1 ]
机构
[1] MIE UNIV,DEPT CHEM MAT,TSU,MIE 514,JAPAN
关键词
D O I
10.1016/S0957-4166(00)80121-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Fluorinated 3-acetoxy-2-(methoxyimino)butyrates were resolved by lipase to give the corresponding alcohols and the acetates in high optical purity. The resolved alcohols were readily converted into mono-, di-, and trifluorothreonine and allo-threonine derivatives by hydrogenation of the methoxyimino group.
引用
收藏
页码:835 / 838
页数:4
相关论文
共 17 条
[1]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299
[2]   ENANTIOSPECIFIC AND DIASTEREOSELECTIVE SYNTHESIS OF ANTI-ALPHA-HYDRAZINO-BETA-HYDROXYACIDS AND ALPHA-AMINO-BETA-HYDROXYACIDS THROUGH ELECTROPHILIC AMINATION OF BETA-HYDROXYESTERS [J].
GUANTI, G ;
BANFI, L ;
NARISANO, E .
TETRAHEDRON, 1988, 44 (17) :5553-5562
[3]  
Hartung W. H., 1973, ORG SYNTH, VV, P376
[4]  
ITSUNO S, 1988, SYNTHESIS-STUTTGART, P995
[5]   ASYMMETRICAL REDUCTION OF PERFLUOROALKYLATED KETONES, KETOESTERS AND VINYL COMPOUNDS WITH BAKERS-YEAST [J].
KITAZUME, T ;
ISHIKAWA, N .
CHEMISTRY LETTERS, 1983, (02) :237-238
[6]  
KITAZUME T, 1991, TETRAHEDRON-ASYMMETR, V4, P235
[7]   FLUORODESULFURIZATION - NEW REACTION FOR FORMATION OF CARBON-FLUORINE BONDS [J].
KOLLONITSCH, J ;
MARBURG, S ;
PERKINS, LM .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (19) :3107-3111
[8]   STEREOSELECTIVITY OF THE REDUCTION OF NALTREXONE OXIME WITH BORANE [J].
MOHAMED, MS ;
PORTOGHESE, PS .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (01) :105-106
[9]   BIOSYNTHESIS OF FLUOROTHREONINE AND FLUOROACETIC ACID BY THE THIENAMYCIN PRODUCER, STREPTOMYCES-CATTLEYA [J].
SANADA, M ;
MIYANO, T ;
IWADARE, S ;
WILLIAMSON, JM ;
ARISON, BH ;
SMITH, JL ;
DOUGLAS, AW ;
LIESCH, JM ;
INAMINE, E .
JOURNAL OF ANTIBIOTICS, 1986, 39 (02) :259-265
[10]  
SCOLASTICO C, 1985, SYNTHESIS-STUTTGART, P850