Two-way homologation of aliphatic aldehydes: Both one-carbon shortening and lengthening via the same intermediate

被引：5

作者：

Yoo, Jae Won ^{[1
]}

Seo, Youngran ^{[1
]}

Park, Jong Beom ^{[1
]}

Kim, Young Gyu ^{[1
]}

机构：

[1] Seoul Natl Univ, Inst Chem Proc, Dept Chem & Biol Engn, Seoul 151744, South Korea

来源：

TETRAHEDRON | 2020年 / 76卷 / 06期

基金：

新加坡国家研究基金会;

关键词：

Two-way homologation; Phenylsulfonylnitromethane; Aliphatic aldehydes; One-carbon shortening; One-carbon lengthening; CARBOXYLIC-ACIDS; ENANTIOSELECTIVE SYNTHESIS; SELECTIVE REDUCTION; ARYL ALDEHYDES; AROMATIC NITROCOMPOUNDS; STANNOUS CHLORIDE; HYDROGEN-TRANSFER; EFFICIENT METHOD; NITRO-COMPOUNDS; KETONES;

D O I：

10.1016/j.tet.2019.130883

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aliphatic aldehydes can be homologated to both one-carbon shorter and one-carbon longer homologous carbonyl compounds through the 2-4 steps of reactions via the same intermediates, beta,gamma-unsaturated alpha-nitrosulfones, prepared from the proline-catalyzed sequential reactions of several aliphatic aldehydes with phenylsulfonylnitromethane. While the oxidative cleavage of the key intermediates gave one-carbon less homologous carbonyl compounds, the reduction of the same key intermediates followed by an oxidation produced one-carbon more homologous carbonyl compounds. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页数：13