Naphthalene-catalysed lithiation of 2-(chlorophenyl)-1,3-dioxolanes:: Generation of formyl- and acetyl-phenyllithium equivalents [1]

被引：13

作者：

Huerta, FF ^{[1
]}

Gómez, C ^{[1
]}

Yus, M ^{[1
]}

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain

来源：

TETRAHEDRON | 1999年 / 55卷 / 13期

关键词：

lithiation; dioxolanes; catalysis; lithium and compounds;

D O I：

10.1016/S0040-4020(99)00092-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 2-(chlorophenyl)-l,3-dioxolanes 1 with an excess of lithium powder and a catalytic amount of naphthalene (5 mol %) in the presence of different carbonyl compounds [(BuCHO)-Bu-t, Et2CO, (CH2)(5)CO, PhCOMe] as electrophiles (Barbier-type conditions) in THF at -78 degrees C leads, after hydrolysis with water at the same temperature, to the expected products 3, the corresponding intermediates involved being formyl- or acetyl phenyl anion equivalents, (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4043 / 4050

页数：8

共 26 条

[1] alpha-nitrogenated organolithium compounds from alpha-amidomethyl and alpha-aminomethyl sulfones [J].

Alonso, DA ;

Alonso, E ;

Najera, C ;

Ramon, DJ ;

Yus, M .

TETRAHEDRON, 1997, 53 (13) :4835-4856

[2]

Alonso F, 1997, RRD ORG CHEM, V1, P397

[3] 2-chloromethyl-3-(2-methoxyethoxy)propene: Naphthalene-catalysed lithiation and reaction towards electrophiles [J].

Alonso, F ;

Lorenzo, E ;

Yus, M .

TETRAHEDRON LETTERS, 1998, 39 (20) :3303-3306

[4] Ketalised alpha- and beta-lithiated alpha,beta-unsaturated ketones: New masked acylvinyl anion equivalents [J].

Bachki, A ;

Foubelo, F ;

Yus, M .

TETRAHEDRON, 1997, 53 (13) :4921-4934

[5] 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

[6] Enantiomerically pure gamma-oxidofunctionalised organolithium compounds from chiral oxetanes [J].

Bachki, A ;

Falvello, LR ;

Foubelo, F ;

Yus, M .

TETRAHEDRON-ASYMMETRY, 1997, 8 (15) :2633-2643

[7]

Blomberg C., 1993, The Barbier reaction and related one-step processes

[8]

DAIGNAULT RA, 1973, ORG SYNTH, V5, P303

[9] SUBSTITUENT EFFECTS IN ACETAL HYDROLYSIS [J].

FIFE, TH ;

JAO, LK .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (05) :1492-&

[10] NEW MASKED DELTA-LITHIOCARBONYL COMPOUNDS - PREPARATION AND SYNTHETIC APPLICATIONS [J].

GIL, JF ;

RAMON, DJ ;

YUS, M .

TETRAHEDRON, 1993, 49 (22) :4923-4938

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