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RESEARCH PRODUCT
Recent Developments in the Chiral Brønsted Acid-catalyzed Allylboration Reaction with Polyfunctionalized Substrates
Elsa RodríguezPablo BarrioSantos Fusterosubject
chemistry.chemical_classification010405 organic chemistryChemistryGeneral Chemical Engineeringasymmetric allylborationTotal synthesisGeneral Chemistry010402 general chemistry01 natural sciencesBiochemistryAldehyde0104 chemical sciencesCatalysischiral BrOnsted acid catalysischemistry.chemical_compounddensity functional calculationsMaterials ChemistryOrganic chemistryOrganic synthesisdiversity-oriented synthesisBrønsted–Lowry acid–base theoryallylic compoundsdescription
Asymmetric allylboration has played a central role in organic synthesis ever since the pioneering work by Hoffman and Brown, having found applications in the total synthesis of many natural products. A new dawn for this 40 year-old reaction occurred with the beginning of the new century when the first catalytic asymmetric methods came into play. In less than one decade, several methodologies, able to achieve the desired homoallylic alcohols with ee ranges in the high 90s, were developed. Among them, in the present account, we will disclose our contribution to the development of the chiral binolphosphoric-derived BrOnsted acid-catalyzed allylboration of aldehydes originally reported by Antilla in 2010. Our contribution to this field lies in its application to polyfunctionalized systems, both on the aldehyde and the allylboronate in question, which enables the rapid construction of molecular diversity and complexity. Parts of the work described herein have been carried out in collaboration with the groups of Profs. Akiyama and Houk.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-01-01 | The Chemical Record |