DISPIROKETALS IN SYNTHESIS .10 - FURTHER REACTIONS OF DISPOKE PROTECTED LACTATE AND GLYCOLATE ENOLATES

被引：34

作者：

BOONS, GJ ^{[1
]}

DOWNHAM, R ^{[1
]}

KIM, KS ^{[1
]}

LEY, SV ^{[1
]}

WOODS, M ^{[1
]}

机构：

[1] UNIV CAMBRIDGE,DEPT CHEM,CAMBRIDGE CB2 1EW,ENGLAND

来源：

TETRAHEDRON | 1994年 / 50卷 / 24期

关键词：

D O I：

10.1016/S0040-4020(01)85241-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Hydroxy acids have been reacted with bis-dihydropyrans to give dispiroketal adducts (1,8,13,16-tetraoxadispiro[5.0.5.4]-hexadecan-14-ones). The enolates derived from these compound undergo reaction with electrophiles with generally high levels of diastereoselectivity. Subsequent deprotection of these compounds gives alpha-hydroxy esters of high enantiomeric excess.

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页码：7157 / 7176

页数：20

相关论文

共 12 条

[1]

BOONS GJ, 1993, TETRAHEDRON LETT, V34, P5649

[2] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[3] THE RESOLUTION AND REACTIONS OF TERTIARY ALCOHOLS - 2 DISUBSTITUTED GLYCOLLIC ACIDS AND THE CORRESPONDING DISUBSTITUTED GLYCOLS [J].

DAVIS, AG ;

EBEID, FM ;

KENYON, J .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (JUL) :3154-3157

[4] DISPIROKETALS IN SYNTHESIS .6. HIGHLY STEREOSELECTIVE ALKYLATION OF DISPIROKETAL PROTECTED LACTATE AND GLYCOLATE ENOLATES [J].

DOWNHAM, R ;

KIM, KS ;

LEY, SV ;

WOODS, M .

TETRAHEDRON LETTERS, 1994, 35 (05) :769-772

[5]

EDWARDS PJ, 1994, IN PRESS TETRAHEDRON

[6] ACYCLIC STEREOSELECTION .4. ASSIGNMENT OF STEREOSTRUCTURE TO BETA-HYDROXYCARBONYL COMPOUNDS BY C-13 NUCLEAR MAGNETIC-RESONANCE [J].

HEATHCOCK, CH ;

PIRRUNG, MC ;

SOHN, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (24) :4294-4299

[7] NEW EPOXIDATION WITH M-CHLOROPERBENZOIC ACID AT ELEVATED-TEMPERATURES [J].

KISHI, Y ;

SUGIURA, S ;

TANINO, H ;

GOTO, T ;

ARATANI, M ;

KAKOI, H ;

INOUE, S ;

FUKUYAMA, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (02) :64-&

[8]

KOBAYASHI M, 1972, CHEM PHARM BULL, V20, P1898

[9] SUBSTITUTION OF HMPT BY THE CYCLIC UREA DMPU AS A COSOLVENT FOR HIGHLY REACTIVE NUCLEOPHILES AND BASES [J].

MUKHOPADHYAY, T ;

SEEBACH, D .

HELVETICA CHIMICA ACTA, 1982, 65 (01) :385-391

[10] ALPHA-ALKYLATION OF ALPHA-HETEROSUBSTITUTED CARBOXYLIC-ACIDS WITHOUT RACEMIZATION - EPC-SYNTHESES OF TERTIARY ALCOHOLS AND THIOLS [J].

SEEBACH, D ;

NAEF, R ;

CALDERARI, G .

TETRAHEDRON, 1984, 40 (08) :1313-1324