CHIRAL BETA-OXIDOFUNCTIONALISED ORGANOLITHIUM COMPOUNDS FROM EPOXIDES - EPC-SYNTHESIS OF 1,3-DIOLS

被引：35

作者：

BACHKI, A ^{[1
]}

FOUBELO, F ^{[1
]}

YUS, M ^{[1
]}

机构：

[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,E-03080 ALACANT,SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 08期

关键词：

D O I：

10.1016/0957-4166(95)00249-O

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The reductive opening of (S)-propylene oxide (I) with lithium powder and a catalytic amount of DTBB (5 mol %) in THF at -78 degrees C followed by treatment with different carbonyl compounds [Bu(t)CHO, PhCHO, (CH2)(5)CO and PhCOMe] at the same temperature leads, after hydrolysis with water to the expected chiral 1,3-diols 3. The same methodology applied to both (R) and(S) protected epoxyalcohols 4 yields the expected enantiomerically pure compounds 6 and 7, wich are monoprotected 1,2,4-triols; carbonation of these last two starting materials affords hydroxyacids 6d and 7d.

引用

页码：1907 / 1910

页数：4

共 16 条

[1] LITHIUM 2-(2-LITHIOMETHYLPHENYL)ETHANOLATE FROM ISOCHROMAN - EASY PREPARATION OF SUBSTITUTED BENZOXEPINES AND FUNCTIONALIZED ARENES [J].

ALMENA, J ;

FOUBELO, F ;

YUS, M .

TETRAHEDRON, 1995, 51 (11) :3365-3374

[2] ARENE-CATALYZED REDUCTIVE DESULFONYLATION AND DESULFINYLATION REACTIONS - NEW ROUTES FOR ALKYLLITHIUMS [J].

ALONSO, E ;

GUIJARRO, D ;

YUS, M .

TETRAHEDRON, 1995, 51 (09) :2699-2708

[3] 2-SUBSTITUTED (E)-2-(2-LITHIOETHENYL)-1,3-DIOXOLANES - NEW DIASTEREOISOMERIC PURE BETA-ACYLVINYL ANION EQUIVALENTS [J].

BACHKI, A ;

FOUBELO, F ;

YUS, M .

TETRAHEDRON LETTERS, 1994, 35 (41) :7643-7646

[4] DIRECT ONE-POT SYNTHESIS OF TERMINAL OLEFINS AND DEUTERIO OLEFINS FROM CARBOXYLIC-ACID CHLORIDES [J].

BARLUENGA, J ;

YUS, M ;

CONCELLON, JM ;

BERNAD, P .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (18) :3116-3118

[5] BETA-SUBSTITUTED ORGANO-LITHIUM COMPOUNDS - REACTION WITH ALKYL-HALIDES, DIMETHYL DISULFIDE, AND IMINES [J].

BARLUENGA, J ;

FANANAS, FJ ;

VILLAMANA, J ;

YUS, M .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (08) :1560-1564

[6] BETA-SUBSTITUTED ORGANO-LITHIUM COMPOUNDS FROM CHLOROHYDRINS - APPLICATION TO THE DIRECT SYNTHESIS OF BIFUNCTIONALIZED ORGANIC-COMPOUNDS [J].

BARLUENGA, J ;

FLOREZ, J ;

YUS, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (12) :3019-3026

[7] SYNTHETICALLY USEFUL BETA-LITHIOALKOXIDES FROM REDUCTIVE LITHIATION OF EPOXIDES BY AROMATIC RADICAL-ANIONS [J].

COHEN, T ;

JEONG, IH ;

MUDRYK, B ;

BHUPATHY, M ;

AWAD, MMA .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1528-1536

[8] A CONVERGENT ROUTE TO CALCITRIOL LACTONE VIA REDUCTIVE CLEAVAGE OF AN ENANTIOPURE GLYCIDYL ETHER [J].

CONROW, RE .

TETRAHEDRON LETTERS, 1993, 34 (35) :5553-5554

[9] SYNTHESIS OF ENANTIOMERICALLY PURE FUNCTIONALIZED AMIDES (EPC-SYNTHESIS) FROM CHIRAL BETA-AMINATED ORGANOLITHIUM INTERMEDIATES [J].

FOUBELO, F ;

YUS, M .

TETRAHEDRON LETTERS, 1994, 35 (27) :4831-4834

[10] DTBB-CATALYZED LITHIATION OF 2,3-DICHLOROPROPENE AND RELATED CHLOROAMINES - SYNTHETIC APPLICATIONS [J].

HUERTA, FF ;

GOMEZ, C ;

GUIJARRO, A ;

YUS, M .

TETRAHEDRON, 1995, 51 (11) :3375-3388

← 1 2 →