title: Diastereoselective ring-closing metathesis: synthesis of P-stereogenic phosphinates from prochiral phosphinic acid derivatives.
abstract: [reaction: see text] The preparation of phosphorus-containing trienes featuring two diastereotopic vinyl moieties followed by a diastereoselective ring-closing metathesis is described. This methodology allowed for the synthesis of novel highly functionalized P-stereogenic heterocycles featuring both an exo- and an endocyclic double bond. An investigation into the factors influencing the diastereochemical outcome of the ring-closing metathesis is also presented, revealing that the geometry of the double bonds conjugated to phosphorus is important and that 1,3-stereoinduction is superior to 1,4-stereoinduction for these reactions.
authors.affiliation: Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK.
authors.forename: Katherine S
authors.initials: KS
authors.lastname: Dunne
authors.forename: Fabrice
authors.initials: F
authors.lastname: Bisaro
authors.forename: Barbara
authors.initials: B
authors.lastname: Odell
authors.forename: Jean-Marc
authors.initials: JM
authors.lastname: Paris
authors.forename: Véronique
authors.initials: V
authors.lastname: Gouverneur