RETRO CLAISEN CLEAVAGE OF ALPHA-NITROCYCLOALKANONES USING TRIMETHYLSILYLMETHYLMAGNESIUM CHLORIDE (PETERSON REAGENT) - SYNTHESIS OF FUNCTIONALIZED BETA-KETO-TRIMETHYLSILANES

被引：13

作者：

BALLINI, R ^{[1
]}

BARTOLI, G ^{[1
]}

GIOVANNINI, R ^{[1
]}

MARCANTONI, E ^{[1
]}

PETRINI, M ^{[1
]}

机构：

[1] UNIV CAMERINO,DIPARTIMENTO SCI CHIM,VIA S AGOSTINO 1,I-62032 CAMERINO,ITALY

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 20期

关键词：

D O I：

10.1016/S0040-4039(00)73688-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Beta-ketosilanes, bearing a nitro functionality, can be prepared by nucleophilic ring cleavage of alpha-nitrocycloalkanones with the Peterson reagent. This high yielding process shows considerable chemoselectivity but fails with large rings (C(n)>7). This unusual reactivity is tentatively explained considering the silicon beta effect.

引用

页码：3301 / 3304

页数：4

共 15 条

[1]

BALLINI R, 1993, IN PRESS J ORG CHEM

[2] STEREOSELECTIVE ALKENE SYNTHESIS VIA (ALPHA-CHLOROALKYL)DIMETHYLPHENYLSILANES AND ALPHA-DIMETHYLPHENYLSILYL KETONES [J].