FLEXIBLE AND STEREOSELECTIVE CONSTRUCTION OF POLYPROPIONATE CHAINS FROM ENANTIOMERICALLY PURE GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED SULFONES

被引：21

作者：

DOMINGUEZ, E ^{[1
]}

CARRETERO, JC ^{[1
]}

机构：

[1] UNIV AUTONOMA MADRID,FAC CIENCIAS,DEPT QUIM,E-28049 MADRID,SPAIN

来源：

TETRAHEDRON | 1994年 / 50卷 / 25期

关键词：

D O I：

10.1016/S0040-4020(01)90483-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Following an homologation sequence the readily available enantiomerically pure gamma-hydroxy vinyl sulfone 2 has been transformed, with complete control of the stereochemistry, into gamma-hydroxy vinyl sulfones of polypropionate structure. The four stereotriads have been prepared by stereoselective additions of organometallics to the vinyl sulfone moiety and by stereoselective reduction of beta-hydroxyketones. In a similar way, these triads are the substrates for the stereoselective introduction of the fourth consecutive asymmetric center.

引用

页码：7557 / 7566

页数：10

共 50 条

[21] ADDITIVE PUMMERER REACTIONS OF VINYLIC SULFOXIDES - SYNTHESIS OF GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED ESTERS AND ALPHA-HYDROXYKETONES [J].

CRAIG, D ;

DANIELS, K ;

MACKENZIE, AR .

TETRAHEDRON LETTERS, 1990, 31 (44) :6441-6444

[22] (Z)-ALPHA-(TRIMETHYLSILYL) ALPHA,BETA-UNSATURATED ESTERS - THEIR STEREOSELECTIVE CONVERSION INTO ALPHA,BETA-UNSATURATED AND BETA,GAMMA-UNSATURATED ESTERS AND BETA,GAMMA-UNSATURATED KETENE ACETALS [J].

NAJAFI, MR ;

WANG, ML ;

ZWEIFEL, G .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2468-2476

[23] EPOXIDATION AND CLEAVAGE OF ALPHA,BETA-UNSATURATED AND BETA,GAMMA-UNSATURATED SULFONES - A KINETIC-STUDY [J].

RAO, DSR .

JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1983, 60 (06) :557-560

[24] A USEFUL PREPARATION OF PYRROLES FROM ALPHA,BETA-UNSATURATED SULFONES [J].

HAAKE, G ;

STRUVE, D ;

MONTFORTS, FP .

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ERICKSON, BW .

ORGANIC SYNTHESES, 1988, 50-9 :683-689

[26] A HIGHLY STEREOSELECTIVE OSMIUM TETROXIDE-CATALYZED HYDROXYLATION OF GAMMA-HYDROXY ALPHA,BETA-UNSATURATED ESTERS [J].

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[27] REGIOSELECTIVE AND STEREOSELECTIVE CYCLOADDITIONS OF NITRONES AND ALPHA,BETA-UNSATURATED GAMMA-LACTAMS [J].

LANGLOIS, N ;

GRIFFARTBRUNET, D ;

VANBAC, N ;

CHIARONI, A ;

RICHE, C .

COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II, 1995, 320 (03) :155-158

[28] HOMOCHIRAL 2,3-EPOXY SULFIDES AS PRECURSORS TO E-GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED SULFOXIDES AND SULFONES [J].

WESTWELL, AD ;

RAYNER, CM .

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[29] Reactivity of lysine moieties toward gamma-hydroxy-alpha,beta-unsaturated epoxides: A model study on protein-lipid oxidation product interaction [J].

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[30] SULFONES .2. ALKENES, DIENES, ALPHA,BETA-UNSATURATED SULFONES, AND MONOSULFONES FROM BETA-DISULFONES [J].

CRONYN, MW ;

ZAVARIN, E .

JOURNAL OF ORGANIC CHEMISTRY, 1954, 19 (02) :139-154

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