title: Michael, Michael-aldol and Michael-Michael reactions of enolate equivalents of butane-2,3-diacetal protected glycolic acid derivatives.
abstract: Consecutive coupling reactions of butane-2,3-diacetal protected glycolic acid derivatives with Michael acceptors and aldehydes are reported. An enantiopure sample of this building block was used to kinetically resolve a chiral Michael acceptor present as a racemic mixture of enantiomers.
authors.affiliation: Department of Chemistry, University of Cambridge, Cambridge, UKCB2 1EW. svl1000@cam.ac.uk
authors.forename: Steven V
authors.initials: SV
authors.lastname: Ley
authors.forename: Darren J
authors.initials: DJ
authors.lastname: Dixon
authors.forename: Richard T
authors.initials: RT
authors.lastname: Guy
authors.forename: Félix
authors.initials: F
authors.lastname: Rodríguez
authors.forename: Tom D
authors.initials: TD
authors.lastname: Sheppard
mesh_terms: D000080:Acetals / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D002073:Butanes / Q000737:chemistry*; D006016:Glycolates / Q000737:chemistry*; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry; D007536:Isomerism; D007700:Kinetics; D008738:Methyl Ethers / Q000737:chemistry
chemical_list: D000080:Acetals; D000447:Aldehydes; D002073:Butanes; D006016:Glycolates; D006573:Heterocyclic Compounds, 1-Ring; D008738:Methyl Ethers; C031149:glycolic acid; C046888:butane; D006859:Hydrogen; C116609:3-hydroxybutanal