Boric acid catalyzed chemoselective esterification of α-hydroxycarboxylic acids

被引：88

作者：

Houston, TA ^{[1
]}

Wilkinson, BL

Blanchfield, JT

机构：

[1] Griffith Univ, Sch Sci, Nathan, Qld 4111, Australia

[2] Univ Queensland, Sch Mol & Microbial Sci, St Lucia, Qld 4072, Australia

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 05期

关键词：

D O I：

10.1021/ol036123g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Boric acid catalyzes the selective esterification of alpha-hydroxycarboxylic acids without causing significant esterification to occur with other carboxylic acids. The procedure is simple, high-yielding, and applicable to the esterification of alpha-hydroxy carboxylates in the presence of other carboxylic acids including beta-hydroxyacids within the same molecule.

引用

收藏

页码：679 / 681

页数：3

相关论文

共 12 条

[1] PREPARATION OF NEW QUINIC ACID BORON ESTERS IN APROTIC MEDIA [J].

FLORESPARRA, A ;

PAREDESTEPOX, C ;

JOSEPHNATHAN, P ;

CONTRERAS, R .

TETRAHEDRON, 1990, 46 (12) :4137-4148

[2] Boronic acid receptors for α-hydroxycarboxylates:: High affinity of Shinkai's glucose receptor for tartrate [J].

Gray, CW ;

Houston, TA .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5426-5428

[3] Direct polycondensation of carboxylic acids and amines catalyzed by 3,4,5-trifluorophenylboronic acid [J].

Ishihara, K ;

Ohara, S ;

Yamamoto, H .

MACROMOLECULES, 2000, 33 (10) :3511-3513

[4] Direct condensation of carboxylic acids with alcohols catalyzed by hafnium(IV) salts [J].

Ishihara, K ;

Ohara, S ;

Yamamoto, H .

SCIENCE, 2000, 290 (5494) :1140-1142

[5] Direct ester condensation from a 1:1 mixture of carboxylic acids and alcohols catalyzed by hafnium(IV) or zirconium(IV) salts [J].

Ishihara, K ;

Nakayama, M ;

Ohara, S ;

Yamamoto, H .

TETRAHEDRON, 2002, 58 (41) :8179-8188

[6]

Latta R, 2001, SYNTHESIS-STUTTGART, P1611

[7]

Lawrence Jr W. W., 1971, TETRAHEDRON LETT, V12, P3453, DOI 10.1016/S0040-4039(01)97203-X

[8] NATURAL FERRIC IONOPHORES - TOTAL SYNTHESIS OF SCHIZOKINEN, SCHIZOKINEN-A, AND ARTHROBACTIN [J].

LEE, BH ;

MILLER, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (01) :24-31

[9] ENANTIOSELECTIVE SYNTHESES OF 3-SUBSTITUTED 4-(ALKOXYCARBONYL)-2-AZETIDINONES FROM MALIC-ACID [J].

MILLER, MJ ;

BAJWA, JS ;

MATTINGLY, PG ;

PETERSON, K .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (25) :4928-4933

[10] COMPLETE IONIZATION SCHEME FOR CITRIC-ACID [J].

PEARCE, KN ;

CREAMER, LK .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1975, 28 (11) :2409-2415