A highly stereoselective entry to α-hydroxy carboxylic acids using D-fructose diacetonide as a chiral auxiliary

被引:23
作者
Yu, HW [1 ]
Ballard, E [1 ]
Wang, BH [1 ]
机构
[1] N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
关键词
D O I
10.1016/S0040-4039(01)00043-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Protected alpha -hydroxy carboxylic acids were synthesized in moderate yield and high diastereoselectivity by alkylation of glycolate ester enolates using a D-fructose-derived chiral auxiliary. The new chiral center was assigned the (R)-configuration based upon comparisons to the literature. Both enantiomers of the auxiliary are readily available. (C) 2001 Published by Elsevier Science Ltd.
引用
收藏
页码:1835 / 1838
页数:4
相关论文
共 48 条
[1]   Enzymatic resolution of chiral 2-hydroxy carboxylic acids by enantioselective oxidation with molecular oxygen catalyzed by the glycolate oxidase from spinach (Spinacia oleracea) [J].
Adam, W ;
Lazarus, M ;
Boss, B ;
SahaMoller, CR ;
Humpf, HU ;
Schreier, P .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7841-7843
[2]  
ADAM W, 1978, SYNTHESIS-STUTTGART, P828
[3]   trans-1,3-dithiane-1,3-dioxide; a chiral acyl anion equivalent. Enantioselective synthesis of alpha-hydroxy- carboxylic acids, esters, amides and ketones [J].
Aggarwal, VK ;
Thomas, A ;
Schade, S .
TETRAHEDRON, 1997, 53 (48) :16213-16228
[4]  
Aladro FJ, 2000, TETRAHEDRON LETT, V41, P3209
[5]   DIASTEREOSELECTIVITY IN THE O-H INSERTION REACTIONS OF RHODIUM CARBENOIDS DERIVED FROM PHENYLDIAZOACETATES OF CHIRAL ALCOHOLS - PREPARATION OF ALPHA-HYDROXY AND ALPHA-ALKOXY ESTERS [J].
ALLER, E ;
BROWN, DS ;
COX, GG ;
MILLER, DJ ;
MOODY, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (14) :4449-4460
[6]   SYNTHESIS OF ANALOGS OF 1,3-DIHYDROXYACETONE PHOSPHATE AND GLYCERALDEHYDE-3-PHOSPHATE FOR USE IN STUDIES OF FRUCTOSE-1,6-DIPHOSPHATE ALDOLASE [J].
BISCHOFBERGER, N ;
WALDMANN, H ;
SAITO, T ;
SIMON, ES ;
LEES, W ;
BEDNARSKI, MD ;
WHITESIDES, GM .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) :3457-3465
[7]   ASYMMETRIC REDUCTION OF ALPHA-KETO ESTERS WITH POTASSIUM 9-O-(1,2-5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSYL)-9-BORATABICYCLO[3.3.1]NONANE - CHIRAL SYNTHESIS OF ALPHA-HYDROXY ESTERS WITH OPTICAL PURITY APPROACHING 100-PERCENT EE [J].
BROWN, HC ;
CHO, BT ;
PARK, WS .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (17) :3396-3398
[8]   Rh-DuPHOS-catalyzed enantioselective hydrogenation of enol esters.: Application to the synthesis of highly enantioenriched α-hydroxy esters and 1,2-diols [J].
Burk, MJ ;
Kalberg, CS ;
Pizzano, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) :4345-4353
[9]   HIGHLY DIASTEREOSELECTIVE REDUCTION OF NEW CHIRAL ALPHA-KETOAMIDES [J].
BYUN, IS ;
KIM, YH .
SYNTHETIC COMMUNICATIONS, 1995, 25 (13) :1963-1969
[10]   ENANTIOSELECTIVE SYNTHESIS OF 2-BENZYLOXY ALCOHOLS AND 1,2-DIOLS VIA ALKYLATION OF CHIRAL GLYCOLATE IMIDES - A CONVENIENT APPROACH TO OPTICALLY-ACTIVE GLYCEROL DERIVATIVES [J].
CARDILLO, G ;
ORENA, M ;
ROMERO, M ;
SANDRI, S .
TETRAHEDRON, 1989, 45 (05) :1501-1508