Influence of β-Substituents in Aldol Reactions of Boron Enolates of β-Alkoxy Methylketones

被引：12

作者：

Dias, Luiz C. ^{[1
]}

de Lucca, Emilio C., Jr. ^{[1
]}

Ferreira, Marco A. B. ^{[1
]}

Garcia, Danilo C. ^{[1
]}

Tormena, Claudio F. ^{[1
]}

机构：

[1] Univ Estadual Campinas, UNICAMP, Inst Quim, BR-13084971 Campinas, SP, Brazil

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 21期

基金：

巴西圣保罗研究基金会;

关键词：

OXYGENATED METHYL KETONES; 1,5-ASYMMETRIC INDUCTION; ADDITION-REACTIONS; 1,5-ANTI STEREOINDUCTION; SILVER TRIFLATE; APRATOXIN-A; FRAGMENT; ALDEHYDES; REMOTE; (+)-ROXATICIN;

D O I：

10.1021/ol102303p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Moderate to good levels of substrate-based 1,5-syn-stereocontrol could be achieved in the boron-mediated aldol reactions of beta-tert-butyl methylketones with achiral aldehydes, independent of the nature of the beta-alkoxy protecting group (P = PMB or TBS). The analysis of the relative energies of the transition structures by theoretical calculations using the density functional B3LYP shows relative energies favoring the corresponding OUT-1,5-SYN transition structures, explaining the observed 1,5-syn stereoinduction.

引用

页码：5056 / 5059

页数：4

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