Highly selective acetate aldol additions using mesityl-substituted chiral auxiliaries.
[reaction: see text] Highly diastereoselective acetate aldol additions using chlorotitanium enolates of mesityl-substituted N-acetyloxazolidinethione and N-acetylthiazolidinethione auxiliaries are reported. These additions proceed in high yields and diastereoselectivities (93:7 to 98:2) for aliphatic, aromatic, and ,-unsaturated aldehydes. Double diastereoselective acetate aldol additions are also reported and are found to proceed in high yields and diastereoselectivities (90:10 to 97:3).
Crimmins
Michael T
MT
Kenan and Venable Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, USA. crimmins@email.unc.edu
Shamszad
Mariam
M
D000085:Acetates / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry; D013237:Stereoisomerism; D053778:Thiazolidines / Q000737:chemistry
D000085:Acetates; D000447:Aldehydes; D023303:Oxazolidinones; D053778:Thiazolidines; C033089:thiazoline-2-thione; C116609:3-hydroxybutanal