ENZYME CATALYZED MONOHYDROLYSIS OF 2-ARYL-1,3-PROPANEDIOL DIACETATES - A STUDY OF STRUCTURAL EFFECTS OF THE ARYL MOIETY ON THE ENANTIOSELECTIVITY

被引:59
作者
GUANTI, G
NARISANO, E
PODGORSKI, T
THEA, S
WILLIAMS, A
机构
[1] CNR,CTR STUDIO DIARILOIDI,I-16132 GENOA,ITALY
[2] UNIV KENT,CHEM LABS,CANTERBURY CT2 7NH,KENT,ENGLAND
关键词
D O I
10.1016/S0040-4020(01)87892-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
PPL catalyzed monohydrolysis of 2-aryl substituted 13-propanediol diacetates afforded the corresponding monoacetates in acceptable to fair chemical and optical yields. Electronic effects in the aromatic ring were examined. Elaboration of some 2-arylpropanediol monoacetates to optically active 2-arylpropanols and propanoic acids was performed. © 1990.
引用
收藏
页码:7081 / 7092
页数:12
相关论文
共 40 条
[31]   PERSPECTIVES IN NONSTEROIDAL ANTIINFLAMMATORY AGENTS [J].
SHEN, TY .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1972, 11 (06) :460-&
[32]  
STAUB H, 1942, HELV CHIM ACTA, V15, P649
[33]   RAPID CHROMATOGRAPHIC TECHNIQUE FOR PREPARATIVE SEPARATIONS WITH MODERATE RESOLUTION [J].
STILL, WC ;
KAHN, M ;
MITRA, A .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (14) :2923-2925
[34]  
SUNJIC V, 1989, GAZZ CHIM ITAL, V119, P229
[35]   REDUCTIVE PINACOL-TYPE REARRANGEMENT OF CHIRAL ALPHA-MESYLOXY KETONES PROMOTED BY ORGANO-ALUMINUM COMPOUNDS [J].
SUZUKI, K ;
KATAYAMA, E ;
MATSUMOTO, T ;
TSUCHIHASHI, G .
TETRAHEDRON LETTERS, 1984, 25 (34) :3715-3718
[36]  
TABER DF, 1985, J AM CHEM SOC, V107, P196, DOI 10.1021/ja00287a035
[37]   ENANTIODIVERGENT ROUTE TO THE AROMATIC BISABOLANE SESQUITERPENES BY REGIO-CONTROLLED AND STEREO-CONTROLLED EPOXIDE OPENING [J].
TAKANO, S ;
YANASE, M ;
SUGIHARA, T ;
OGASAWARA, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (23) :1538-1540
[38]   SYNTHESIS OF BOTH ENANTIOMERIC FORMS OF 2-SUBSTITUTED 1,3-PROPANEDIOL MONOACETATES STARTING FROM A COMMON PROCHIRAL PRECURSOR, USING ENZYMATIC TRANSFORMATIONS IN AQUEOUS AND IN ORGANIC MEDIA [J].
TOMBO, GMR ;
SCHAR, HP ;
FERNANDEZ, X ;
BUSQUETS, I ;
GHISALBA, O .
TETRAHEDRON LETTERS, 1986, 27 (47) :5707-5710
[39]   BIFUNCTIONAL CHIRAL SYNTHONS VIA BIOCHEMICAL METHODS .4. CHIRAL PRECURSORS TO (+)-BIOTIN AND (-)-A-FACTOR [J].
WANG, YF ;
SIH, CJ .
TETRAHEDRON LETTERS, 1984, 25 (44) :4999-5002
[40]   DISIC ACIDS - STUDY OF A NEW SERIES OF STRONG ORGANIC-ACIDS AND THEIR CONDENSATION PRODUCTS WITH ALDEHYDES [J].
ZVILICHOVSKY, G .
TETRAHEDRON, 1975, 31 (16) :1861-1867