title: Amphoteric α-boryl aldehydes.
abstract: A new class of stable molecules, α-boryl aldehydes, has been prepared from oxiranyl N-methyliminodiacetyl boronates by a 1,2-boryl migration with concomitant epoxide scission. A range of boryl imines, alkenes, alcohols, acids, enol ethers, enamides, and other functionalized boronic acid derivatives that are difficult or impossible to prepare using established protocols can be accessed from α-boryl aldehydes. The chemoselective transformations of these building blocks, including the facile synthesis of functionalized unnatural amino acids from silyloxy and amido vinyl boronates, attest to the potential of α-boryl aldehydes in chemical synthesis.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto, Ontario, Canada.
authors.forename: Zhi
authors.initials: Z
authors.lastname: He
authors.forename: Andrei K
authors.initials: AK
authors.lastname: Yudin