Double diastereoselective SuperQuat glycolate aldol reactions: application to the asymmetric synthesis of polyfunctionalised lactones.
Polyfunctionalised lactones with up to five contiguous stereocentres may be prepared with high stereocontrol by a double diastereoselective aldol protocol with protected homochiral alpha,beta-dihydroxy- or alpha,beta-gamma-trihydroxyaldehydes and a chiral glycolate oxazolidinone, followed by subsequent O-desilylation and lactonisation.
Davies
Stephen G
SG
The Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK. steve.davies@chem.ox.ac.uk
Nicholson
Rebecca L
RL
Smith
Andrew D
AD
D000447:Aldehydes / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D006016:Glycolates / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D008956:Models, Chemical; D013237:Stereoisomerism
D000447:Aldehydes; D006016:Glycolates; D007783:Lactones; C031149:glycolic acid; C116609:3-hydroxybutanal