期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 4, 页码 2148-2154出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo5026354
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资金
- Spanish Ministerio de Economia y Competitividad (MINECO) [CTQ2013-43395-P, CTQ2011-29054-C02-02]
- Generalitat de Catalunya [2009SGR-00259]
- ICIQ Foundation
- Natural Sciences and Engineering Research Council of Canada
- Mount Allison University
- URV-La Caixa
- URV-ICIQ
Herein a direct beta-sulfido carbonyl compound synthesis by the easy activation of RS-Bpin reagents with alpha,beta-unsaturated ketones and aldehydes is reported. This convenient methodology can be performed at room temperature with no other additives. The key point of this reactivity is based on the Lewis acidic properties of the boryl unit of the RS-Bpin reagent interacting with the C=O oxygen. Consequently, the SR unit becomes more nucleophilic and promotes the 1,4- versus the 1,2-addition, as a function of the involved substrate. The thioborated products can be further transformed into beta-sulfido carbonyl compounds by addition of MeOH
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