期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 6, 页码 2943-2956出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02917
关键词
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资金
- JSPS [26288048, 265249]
- MEXT [25105728]
- ACT-C FS from JST
- Grants-in-Aid for Scientific Research [26288048, 25105728, 14J05249] Funding Source: KAKEN
A conversion of trimethylsilylalkanes into the corresponding alcohols is established based on an iridium-catalyzed, chemoselective C(sp(3))-H borylation of the methyl group on silicon. The (borylmethyl)silyl group formed by C(sp(3))-H borylation is treated with H2O2/NaOH, and the resulting (hydroxymethyl)silyl group is converted into a hydroxyl group by Brook rearrangement, followed by oxidation of the resulting methoxysilyl group under Tamao conditions. An alternative route proceeding through the formylsilyl group formed from a (hydroxymethyl)silyl group by Swern oxidation is also established. The method is applicable to substituted trimethylsilylcycloalkanes and 1,1-dimethyl-l-silacyclopentane for conversion into the corresponding stereodefined cycloalkyl alcohols and 1,4-butanediol.
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