CONVENIENT SYNTHESIS OF ALPHA-HETERO-SUBSTITUTED ACYLOXATHIANES

被引：6

作者：

BAI, X ^{[1
]}

ELIEL, EL ^{[1
]}

机构：

[1] UNIV N CAROLINA,DEPT CHEM,WR KENAN JR LABS,CHAPEL HILL,NC 27599

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 19期

关键词：

D O I：

10.1021/jo00045a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In contrast to simple esters, alpha-alkoxy, alpha-alkylthio, and alpha-dimethylamino esters react with lithiooxathiane 1-Li in good yield to give the corresponding alpha-functionalized 2-acetylhexahydro-4,4,7-trimethyl-4H-1,3-benzoxathiin 2. In some cases, mixtures of diastereomers (2, 2') are obtained. The reaction has been extended to alpha-methoxy- and alpha-[(triisopropylsilyl)oxy]propanoyl and alpha-(methylthio)butanoyl homologs which have chiral centers at C(alpha).

引用

页码：5162 / 5166

页数：5

共 11 条

[1]

BAI X, 1992, J ORG CHEM, V57

[2] ELECTROCHEMICAL OXIDATION OF ALKYL-SUBSTITUTED ALLENES IN METHANOL [J].

BECKER, JY ;

ZINGER, B .

TETRAHEDRON, 1982, 38 (11) :1677-1682

[3] THE TRIISOPROPYLSILYL GROUP AS A HYDROXYL-PROTECTING FUNCTION [J].

CUNICO, RF ;

BEDELL, L .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) :4797-4798

[4] AN IMPROVED SYNTHESIS OF 2-OXATHIANYL KETONES [J].

ELIEL, EL ;

BAI, X ;

ABDELMAGID, AF ;

HUTCHINS, RO .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (16) :4951-4953

[5]

ELIEL EL, 1987, ORG SYNTH, V65, P215

[6]

ELIEL EL, 1974, J AM CHEM SOC, V96, P1087

[7] ASYMMETRIC-SYNTHESIS BASED ON 1,3-OXATHIANES .4. MECHANISM OF ASYMMETRIC INDUCTION IN THE REACTIONS OF OXATHIANYL KETONES [J].

FRYE, SV ;

ELIEL, EL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) :484-489

[8]

Levene PA, 1933, J BIOL CHEM, V102, P297

[9] ASYMMETRIC SYNTHESES BASED ON 1,3-OXATHIANES .2. SYNTHESIS OF CHIRAL TERTIARY ALPHA-HYDROXY ALDEHYDES, ALPHA-HYDROXY ACIDS, GLYCOLS (RR'C(OH)CH2OH), AND CARBINOLS (RR'C(OH)CH3) IN HIGH ENANTIOMERIC PURITY [J].

LYNCH, JE ;

ELIEL, EL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (10) :2943-2948

[10]

LYNCH JE, 1982, THESIS U N CARLOINA, P40

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