DIRECT TRANSFORMATION OF DIALKYL SULFATES INTO ALKYLLITHIUM REAGENTS BY A NAPHTHALENE-CATALYZED LITHIATION

被引：29

作者：

GUIJARRO, D ^{[1
]}

GUILLENA, G ^{[1
]}

MANCHENO, B ^{[1
]}

YUS, M ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1994年 / 50卷 / 11期

关键词：

D O I：

10.1016/S0040-4020(01)87022-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The lithiation of primary and secondary dialkyl sulfates with an excess of lithium powder in the presence of a catalytic amount of naphthalene (4 mol %) in THF at -78 degrees C leads to the corresponding alkyllithium reagents (1:2 molar ratio) which react with different electrophiles, mainly carbonyl compounds, to yield after hydrolysis, the expected coupling products. This methodology represents an indirect way to transform alcohols into organolithium compounds through the corresponding dialkyl sulfates. When the same procedure is applied to five or six member cyclic sulfates (derived from 1,2- or 1,3-diols) only products arising from a beta- or gamma-elimination process (giving olefins or cyclopropanes), respectively, are obtained.

引用

页码：3427 / 3436

页数：10

共 56 条

[21] NAPHTHALENE-CATALYZED LITHIATION OF 3-CHLORO-2-CHLOROMETHYLPROPENE IN A BARBIER-TYPE PROCESS WITH CARBONYL-COMPOUNDS [J].

GOMEZ, C ;

RAMON, DJ ;

YUS, M .

TETRAHEDRON, 1993, 49 (19) :4117-4126

[22]

GREENWOOD FL, 1963, J ORG CHEM, V28, P1159

[23] 4,4'-DI-TERT-BUTYLBIPHENYL-CATALYZED LITHIATION OF 2,3-DICHLOROPROPENE - A BARBIER-TYPE PRACTICAL ALTERNATIVE TO 2,3-DILITHIOPROPENE [J].

GUIJARRO, A ;

YUS, M .

TETRAHEDRON LETTERS, 1993, 34 (12) :2011-2014

[24] NAPHTHALENE-CATALYZED LITHIATION OF FUNCTIONALIZED CHLOROARENES - REGIOSELECTIVE PREPARATION AND REACTIVITY OF FUNCTIONALIZED LITHIOARENES [J].

GUIJARRO, A ;

RAMON, DJ ;

YUS, M .

TETRAHEDRON, 1993, 49 (02) :469-482

[25] 4,4'-DI-TERT-BUTYLBIPHENYL-CATALYZED LITHIATION OF CHLOROMETHYL ETHYL ETHER - A BARBIER-TYPE NEW AND EASY ALTERNATIVE TO ETHYL LITHIOMETHYL ETHER [J].

GUIJARRO, A ;

YUS, M .

TETRAHEDRON LETTERS, 1993, 34 (21) :3487-3490

[26]

GUIJARRO A, IN PRESS TETRAHEDRON

[27] NAPHTHALENE-CATALYZED LITHIATION OF DIALKYL SULFATES - A NEW ROUTE FOR ORGANOLITHIUM REAGENTS [J].

GUIJARRO, D ;

MANCHENO, B ;

YUS, M .

TETRAHEDRON LETTERS, 1992, 33 (38) :5597-5600

[28] NAPHTHALENE-CATALYZED LITHIATION OF ALLYLIC AND BENZYLIC MESYLATES - A NEW METHOD FOR ALLYL, METHALLYL, AND BENZYL LITHIUM [J].

GUIJARRO, D ;

MANCHENO, B ;

YUS, M .

TETRAHEDRON, 1992, 48 (22) :4593-4600

[29] NAPHTHALENE-CATALYZED LITHIATION OF PHENONE IMINES IN THE PRESENCE OF CARBONYL-COMPOUNDS - PREPARATION OF 1,2-AMINOALCOHOLS [J].

GUIJARRO, D ;

YUS, M .

TETRAHEDRON, 1993, 49 (35) :7761-7768

[30] SODIUM DIPHENYLKETYL ALKYLATION BY CHIRAL ELECTROPHILIC REAGENTS [J].

HEBERT, E ;

MAZALEYRAT, JP ;

WELVART, Z .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (23) :877-878

← 1 2 3 4 5 6 →