THE ADDITION OF ALLYLBORONATES TO ALPHA-OXOCARBOXYLIC ACIDS

被引:20
作者
WANG, Z
MENG, XJ
KABALKA, GW
机构
[1] UNIV TENNESSEE,DEPT CHEM,KNOXVILLE,TN 37996
[2] UNIV TENNESSEE,DEPT RADIOL,KNOXVILLE,TN 37996
关键词
D O I
10.1016/S0040-4039(00)92264-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Allylboronates react with alpha-oxocarboxylic acids to yield tertiary homoallylic alpha-hydroxycarboxylic acids in a highly chemoselective manner. The reaction presumably proceeds via a bicyclic transition state. The alpha-carboxylic substituent enhances the rate of the reaction.
引用
收藏
页码:4619 / 4622
页数:4
相关论文
共 38 条
[1]   STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .30. E-PENTENYLBORONATES AND Z-PENTENYLBORONATES, REAGENTS FOR SIMPLE DIASTEREOSELECTION ON ADDITION TO ALDEHYDES [J].
ANDERSEN, MW ;
HILDEBRANDT, B ;
KOSTER, G ;
HOFFMANN, RW .
CHEMISCHE BERICHTE, 1989, 122 (09) :1777-1782
[2]   INHIBITORS OF GASTRIC-ACID SECRETION [J].
BAYS, DE ;
FINCH, H .
NATURAL PRODUCT REPORTS, 1990, 7 (05) :409-445
[4]   CHIRAL SYNTHESIS VIA ORGANOBORANES .24. B-ALLYLBIS(2-ISOCARANYL)BORANE AS A SUPERIOR REAGENT FOR THE ASYMMETRIC ALLYLBORATION OF ALDEHYDES [J].
BROWN, HC ;
RANDAD, RS ;
BHAT, KS ;
ZAIDLEWICZ, M ;
RACHERLA, US .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (06) :2389-2392
[6]   ORGANOBORANES .53. A HIGH-FIELD VARIABLE-TEMPERATURE H-1 AND B-11 NMR-STUDY OF THE EFFECTS OF SOLVENT AND STRUCTURE ON REACTIVITY IN ALLYLBORATION [J].
BROWN, HC ;
RACHERLA, US ;
PELLECHIA, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1868-1874
[7]  
BROWN HC, 1990, TETRAHEDRON LETT, P455
[8]   A PRACTICAL AND GENERAL ENANTIOSELECTIVE SYNTHESIS OF CHIRAL PROPA-1,2-DIENYL AND PROPARGYL CARBINOLS [J].
COREY, EJ ;
YU, CM ;
LEE, DH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) :878-879
[9]   A PRACTICAL AND EFFICIENT METHOD FOR ENANTIOSELECTIVE ALLYLATION OF ALDEHYDES [J].
COREY, EJ ;
YU, CM ;
KIM, SS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5495-5496
[10]   STEREOSELECTIVE SYNTHESES OF ALCOHOLS .33. ADDITION OF E-PENTENYLBORONATES AND Z-PENTENYLBORONATES TO KETONES [J].
HOFFMANN, RW ;
SANDER, T .
CHEMISCHE BERICHTE, 1990, 123 (01) :145-152