REARRANGEMENT OF 2-(ARYLMETHOXY)METHYL-2-OXAZOLINES VIA LITHIUM AZAENOLATES - A FACILE SYNTHETIC ROUTE TO ORTHO-METHYLMANDELIC ACID-DERIVATIVES

被引：1

作者：

KAMATA, K

TERASHIMA, M

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1994年 / 24期

关键词：

D O I：

10.1039/c39940002771

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2-(Arylmethoxy)methyl-2-oxazolines, on treatment with LDA in THF at low temperature, rearrange to afford products which are hydrolysed to ortho-methylmandelic acids or alpha-(1-methyl-2-naphthyl)glycolic acid.

引用

页码：2771 / 2772

页数：2

共 23 条

[1] RESOLUTION OF UNDERIVATIZED 2-HYDROXY ACIDS BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].

BENECKE, I .

JOURNAL OF CHROMATOGRAPHY, 1984, 291 (MAY) :155-164

[2]

BUNCEL E, 1975, CARBANIONS MECHANIST, P197

[3] RESOLUTION OF SOME CHIRAL MANDELIC-ACID DERIVATIVES INTO ENANTIOMERS BY REVERSED-PHASE HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY VIA ALPHA-CYCLODEXTRIN AND BETA-CYCLODEXTRIN INCLUSION COMPLEXES [J].

DEBOWSKI, J ;

JURCZAK, J ;

SYBILSKA, D .

JOURNAL OF CHROMATOGRAPHY, 1983, 282 (DEC) :83-88

[4]

FELKIN H, 1977, TETRAHEDRON LETT, P3485

[5] THE CHEMISTRY OF 2-OXAZOLINES (1985-PRESENT) [J].

GANT, TG ;

MEYERS, AI .

TETRAHEDRON, 1994, 50 (08) :2297-2360

[6] STEREOCHEMISTRY OF [2,3]SIGMATROPIC REARRANGEMENTS [J].

HOFFMANN, RW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (08) :563-572

[7]

JULIA S, 1972, CR ACAD SCI C CHIM, V274, P2019

[8]

KAMATA K, UNPUB

[9] A FACILE CLEAVAGE OF OXAZOLINES TO CARBINOLS [J].

MEYERS, AI ;

SHIMANO, M .

TETRAHEDRON LETTERS, 1993, 34 (31) :4893-4896

[10]

MEYERS AI, 1974, TETRAHEDRON LETT, P3495

← 1 2 3 →