Practical and highly selective oxazolidinethione-based asymmetric acetate aldol reactions with aliphatic aldehydes.
[reaction: see text] The utility of a valine-derived oxazolidinethione for auxiliary-based asymmetric acetate aldol reactions is reported. Titanium(IV) chloride, along with (-)-sparteine and N-methylpyrrolidinone, is employed for enolization. Subsequent aldol reaction with aliphatic aldehydes occurs with high diastereoselectivity (from 92:8 to 99:1 dr).
Guz
Nathan R
NR
Department of Chemistry and Biochemistry, University of Colorado at Boulder, Boulder, Colorado 80309-0215, USA.
Phillips
Andrew J
AJ
D000447:Aldehydes / Q000737:chemistry*; D001685:Biological Factors / Q000138:chemical synthesis*; D010080:Oxazoles / Q000737:chemistry; D013034:Sparteine / Q000737:chemistry; D013237:Stereoisomerism; D013871:Thiones / Q000737:chemistry; D014025:Titanium / Q000737:chemistry
D000447:Aldehydes; D001685:Biological Factors; D010080:Oxazoles; D013871:Thiones; C064210:oxazolidine; D013034:Sparteine; C116609:3-hydroxybutanal; C025096:titanium tetrachloride; D014025:Titanium