Magnesium halide-catalyzed anti-aldol reactions of chiral N-acylthiazolidinethiones.
[reaction: see text] Diastereoselective direct aldol reactions of chiral N-acylthiazolidinethiones occur in high yield with preference for the illustrated anti diastereomer. This reaction is catalyzed by 10% MgBr2.OEt2 in the presence of triethylamine and chlorotrimethylsilane. Yields range from 56 to 93% with diastereoselectivity up to 19:1 for a variety of N-acylthiazolidinethiones and unsaturated aldehydes.
Evans
David A
DA
Department of Chemistry & Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu
Downey
C Wade
CW
Shaw
Jared T
JT
Tedrow
Jason S
JS
D002384:Catalysis; D007202:Indicators and Reagents; D008274:Magnesium; D008958:Models, Molecular; D008968:Molecular Conformation; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
D007202:Indicators and Reagents; D013844:Thiazoles; D008274:Magnesium