Michael, Michael-aldol and Michael-Michael reactions of enolate equivalents of butane-2,3-diacetal protected glycolic acid derivatives.
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.
Ley
Steven V
SV
Department of Chemistry, University of Cambridge, Cambridge, UKCB2 1EW. svl1000@cam.ac.uk
Dixon
Darren J
DJ
Guy
Richard T
RT
Rodríguez
Félix
F
Sheppard
Tom D
TD
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
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