Indium-promoted preparation of substituted α-methylene-γ-lactones from 2-(bromomethyl)acrylic acid and carbonyl compounds

被引：43

作者：

Choudhury, PK ^{[1
]}

Foubelo, F ^{[1
]}

Yus, M ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 21期

关键词：

D O I：

10.1016/S0040-4039(98)00554-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 2-(bromomethyl)acrylic acid (1) with different carbonyl compounds (2) [CH2O, (E)-CH3CH=CHCHO, (PrCHO)-C-i, (BuCHO)-C-t, PhCHO, CH3(CH2)(5)CHO, c-C6H11CHO, Ph2CHCHO, (CH2)(5)CO] and indium powder in a 1:1 THF:H2O mixture at room temperature affords, after acidic work-up with hydrochloric acid, the corresponding alpha-methylene-gamma-butyrolactones 3. (C) 1998 Elsevier Science Ltd, All nights reserved.

引用

页码：3581 / 3584

页数：4

共 19 条

[1] PREPARATION AND SOME REACTIONS OF ALLYLIC INDIUM REAGENTS [J].

ARAKI, S ;

SHIMIZU, T ;

JOHAR, PS ;

JIN, SJ ;

BUTSUGAN, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2538-2542

[2]

ASHIDA K, 1984, JPN J PHARMACOL, V36, pP295

[3]

ASHIDA K, 1982, Japanese Journal of Pharmacology, V32, p183P

[4]

BERGMAN BHH, 1967, RECL TRAV CHIM PAY-B, V86, P709

[5] Stereoselective indium-promoted allylation of gamma-hydroxy-gamma-lactones under aqueous conditions. The neighboring carboxyl effect [J].

Bernardelli, P ;

Paquette, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) :8284-8285

[6]

BRONGERS.UW, 1967, RECL TRAV CHIM PAY-B, V86, P705

[7]

CARLSON RM, 1978, TETRAHEDRON LETT, P111

[8]

CCAVALLITO CJ, 1946, J AM CHEM SOC, V68, P2332

[9]

CINTAS P, 1995, SYNLETT, P1087

[10] PRACTICAL SYNTHESIS OF "ALPHA-METHYLENE-GAMMA-BUTYROLACTONE [J].

GRIECO, PA ;

POGONOWS.CS .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (13) :1958-1959

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