ENANTIOSELECTIVE ACYLATION OF ENOLATES - THE REACTION OF (4R)-TRANS-DIETHYL 2-ALKYL-2-METHOXY-1,3-DIOXOLANE-4,5-DICARBOXYLATES WITH E-SILYL AND Z-SILYL ENOL ETHERS

被引：10

作者：

BASILE, T ^{[1
]}

LONGOBARDO, L ^{[1
]}

TAGLIAVINI, E ^{[1
]}

TROMBINI, C ^{[1
]}

UMANIRONCHI, A ^{[1
]}

机构：

[1] UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,VIA SELMI 2,I-40126 BOLOGNA,ITALY

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1991年 / 06期

关键词：

D O I：

10.1039/c39910000391

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The stereoselectivity of the Lewis acid induced acylation of open-chain silyl enol ethers by chiral orthoesters is strongly affected by the C = C bond configuration: both Z and E silyl enol ethers are acylated in good isolated yields, but the Z isomers give rise to a 1:1 ratio of diastereoisomeric monoprotected 1,3-diketones, while excellent stereoselectivities are obtained with E enols.

引用

页码：391 / 392

页数：2

共 8 条

[1] NOVEL ENANTIOSELECTIVE ACYLATING AGENTS - THE REACTIONS OF CHIRAL ORTHO ESTERS AND SILYLENOL ETHERS AS A ROUTE TO OPTICALLY-ACTIVE MONOPROTECTED 1,3-DICARBONYL COMPOUNDS [J].

BASILE, T ;

LONGOBARDO, L ;

TAGLIAVINI, E ;

TROMBINI, C ;

UMANIRONCHI, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (10) :759-760

[2] PREPARATION OF BETA-KETO ESTER ACETALS BY REACTION OF ORTHO ESTERS WITH KETENE SILYL ACETALS IN THE PRESENCE OF TITANIUM TETRACHLORIDE [J].

COLLINS, DJ ;

CHOO, GLP ;

OBRIST, H .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (03) :617-622

[3] STEREOSELECTIVE AND REGIOSELECTIVE FORMATION OF SILYL ENOL ETHERS VIA OXIDATION OF VINYL ANIONS [J].

DAVIS, FA ;

LAL, GS ;

WEI, J .

TETRAHEDRON LETTERS, 1988, 29 (34) :4269-4272

[4] ASYMMETRIC ACYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - THE 1ST DIRECT APPROACH TO THE CONSTRUCTION OF CHIRAL BETA-DICARBONYL SYNTHONS [J].

EVANS, DA ;

ENNIS, MD ;

LE, T ;

MANDEL, N ;

MANDEL, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (04) :1154-1156

[5] PHEROMONE SYNTHESIS .88. SYNTHESIS OF ALL OF THE 4 POSSIBLE STEREOISOMERS OF 5-HYDROXY-4-METHYL-3-HEPTANONE (SITOPHILURE), THE AGGREGATION PHEROMONE OF THE RICE WEEVIL AND THE MAIZE WEEVIL [J].

MORI, K ;

EBATA, T .

TETRAHEDRON, 1986, 42 (16) :4421-4426

[6]

NAGAO Y, 1988, J ORG CHEM, V53, P5883

[7]

NAKAMURA E, 1978, TETRAHEDRON LETT, V24, P2079

[8] ELECTROPHILIC ALPHA-FORMYLATION OF CARBONYL-COMPOUNDS USING NOR-EPHEDRINE-DERIVED 2-METHOXY OXAZOLIDINES - A NOVEL ASYMMETRIC FORMATION OF QUATERNARY STEREOCENTERS [J].

PALAZZI, C ;

POLI, G ;

SCOLASTICO, C ;

VILLA, R .

TETRAHEDRON LETTERS, 1990, 31 (29) :4223-4226

← 1 →