title: Recent Developments in the Chiral Brønsted Acid-catalyzed Allylboration Reaction with Polyfunctionalized Substrates.
abstract: 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 Brønsted 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.
authors.affiliation: Departamento de Química Orgánica, Universidad de Valencia, Avenida Vicent Andrés Estellés s/n, 46100, Burjassot, Spain.
authors.forename: Pablo
authors.initials: P
authors.lastname: Barrio
authors.affiliation: Departamento de Química Orgánica, Universidad de Valencia, Avenida Vicent Andrés Estellés s/n, 46100, Burjassot, Spain.
authors.forename: Elsa
authors.initials: E
authors.lastname: Rodríguez
authors.affiliation: Departamento de Química Orgánica, Universidad de Valencia, Avenida Vicent Andrés Estellés s/n, 46100, Burjassot, Spain.|Laboratorio de Moléculas Orgánicas, Centro de Investigación "Príncipe Felipe", 46012, Valencia, Spain.
authors.forename: Santos
authors.initials: S
authors.lastname: Fustero
keywords: allylic compounds; asymmetric allylboration; chiral Brønsted acid catalysis; density functional calculations; diversity-oriented synthesis