Stereocontrolled synthesis of 5-(1′-hydroxyalkyl)-3-methylidenetetrahydro-2-furanones

被引:13
作者
Janecki, T [1 ]
Blaszczyk, E [1 ]
机构
[1] Lodz Tech Univ, Inst Organ Chem, PL-90924 Lodz, Poland
关键词
Horner-Wadsworth-Emmons olefination; 2-furanones; diastereoselection; enantioselection;
D O I
10.1016/S0040-4039(01)00316-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diastereo- and enantioselective synthesis of 5-(1 ' -hydroxyalkyl)-3-methylidenetetrahydro-2-furanones from 2-diethoxyphosphoryl-4-alkenoic acids or 2-diethoxyphosphoryl-4-alkenoates was readily accomplished using novel methodology involving syn- or anti-dihydroxylation procedures combined with Horner-Wadsworth-Emmons olefination techniques. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2919 / 2922
页数:4
相关论文
共 20 条
[1]   ALLERGENIC ALPHA-METHYLENE-GAMMA-BUTYROLACTONES - BETA-HYDROXY-ALPHA-METHYLENE-GAMMA-BUTYROLACTONES .2. SYNTHESES FROM ETHYL 2-(PHENYLTHIO)PROPIONATE AND ALPHA-ACETOXY ALDEHYDES [J].
BARBIER, P ;
BENEZRA, C .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (16) :2705-2709
[2]   SYNTHETIC OPPORTUNITIES OFFERED BY ANTI ALPHA-METHYLENE-BETA-HYDROXY-GAMMA-ALKOXY ESTERS - STEREOSELECTIVE REACTIONS AT THE DOUBLE-BOND [J].
BERNARDI, A ;
BERETTA, MG ;
COLOMBO, L ;
GENNARI, C ;
POLI, G ;
SCOLASTICO, C .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) :4442-4447
[3]   SYNTHESIS OF AN OPTICALLY-ACTIVE ALPHA-METHYLENE LACTONE STARTING FROM ISOSACCHARINIC ACID [J].
BOCK, K ;
CASTILLA, IM ;
LUNDT, I ;
PEDERSEN, C .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1987, 41 (01) :13-17
[4]  
FIESER LF, 1967, REAGENTS ORGANIC SYN, P796
[5]   SYNTHESIS AND BIOLOGICAL-ACTIVITY OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES [J].
HOFFMANN, HMR ;
RABE, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (02) :94-110
[6]   Experimental test of setting three contiguous stereogenic centers in water. Diastereoselective coupling of geometrically biased allylic bromides to alpha-oxy aldehydes with indium [J].
Isaac, MB ;
Paquette, LA .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5333-5338
[7]  
Janecki T, 2001, SYNTHESIS-STUTTGART, P403
[8]  
Janecki T, 2000, SYNLETT, P611
[9]   CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].
KOLB, HC ;
VANNIEUWENHZE, MS ;
SHARPLESS, KB .
CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547
[10]   PALLADIUM-CATALYZED CARBONYLATION OF VINYL HALIDES - A ROUTE TO THE SYNTHESIS OF ALPHA-METHYLENE LACTONES [J].
MARTIN, LD ;
STILLE, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (19) :3630-3633