Stereodivergent synthesis of 1,3-syn- and -anti-tetrahydropyrimidinones.
An efficient protocol for the stereoselective synthesis of 1,3-syn and -anti-tetrahydropyrimidinones (syn- and anti-11a) is reported. The modular procedure is based on a stereodivergent cyclization of readily available urea-type substrates (10a) by intramolecular allylic substitution. The cyclization proceeds with excellent yield (up to 99%) and selectivity (up to dr > 20:1), purely based on substrate control. The product pyrimidines can be readily transformed into the corresponding free syn- and anti-amines.
Morgen
Michael
M
University of Heidelberg, Department of Organic Chemistry, INF 270, D-69120 Heidelberg, Germany.
Bretzke
Sebastian
S
Li
Pengfei
P
Menche
Dirk
D
D003500:Cyclization; D015394:Molecular Structure; D011744:Pyrimidinones / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014508:Urea / Q000737:chemistry
D011744:Pyrimidinones; C505709:tetrahydropyrimidinone; D014508:Urea