title: Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins.
abstract: The diastereoselective Ireland-Claisen rearrangement of a range of substituted allyl β-amino esters gave the corresponding enantiopure α-substituted-β-amino esters with good diastereoselectivity. The application of this methodology in the asymmetric synthesis of a range of C(5)-substituted 1,2-anti-1,5-syn-transpentacins was demonstrated by the rearrangement of a range of β-amino esters derived from sorbic acid, followed by esterification, ring-closing metathesis, hydrogenolytic deprotection/reduction, and hydrolysis, which gave the C(5)-substituted transpentacins in only 9 steps from commercially available starting materials.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK. steve.davies@chem.ox.ac.uk.
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Davies
authors.forename: Ai M
authors.initials: AM
authors.lastname: Fletcher
authors.forename: James A
authors.initials: JA
authors.lastname: Lee
authors.forename: Paul M
authors.initials: PM
authors.lastname: Roberts
authors.forename: Myriam Y
authors.initials: MY
authors.lastname: Souleymanou
authors.forename: James E
authors.initials: JE
authors.lastname: Thomson
authors.forename: Charlotte M
authors.initials: CM
authors.lastname: Zammit