title: Achieving high selectivity and facile displacement with a new thiol auxiliary for boron-mediated aldol reactions.
abstract: Synthesis of a new thiol auxiliary (1) is readily achieved (in five or six steps, >74% overall yield from norephedrine) and is shown to give high diastereoselectivity in boron-mediated anti-aldol reactions with a range of aldehydes. This new thiol auxiliary may be directly displaced by a range of nucleophiles under very mild conditions, to give the corresponding phosphonate esters, alcohols, acids, SNAC thiolesters, and methyl esters.
authors.affiliation: School of Chemistry, University of Edinburgh, West Mains Road, Edinburgh EH9 3JJ, UK.
authors.forename: Sandra
authors.initials: S
authors.lastname: Fanjul
authors.forename: Alison N
authors.initials: AN
authors.lastname: Hulme
authors.forename: John W
authors.initials: JW
authors.lastname: White