S. Onogi, Shuhei Higashibayashi, H. Sakurai
Jul 18, 2012
Citations
0
Influential Citations
2
Citations
Journal
Tetrahedron Letters
Abstract
Abstract Methyl (1 S ,2 R ,4 S ,5 R )-7-aza-5-bromo-bicyclo[2.2.1]heptane-2-carboxylate was synthesized in high yield in short time from methyl (1 R ,2 S ,4 R ,5 R )-2-amino-4,5-dibromocyclohexanecarboxylate through intramolecular cycloamination under microwave-assisted conditions. The following substitution reaction by trifluoro-acetate anion also took place in microwave-assisted conditions to afford methyl (1 S ,2 R ,4 S ,5 S )-7-aza-5-hydroxy-bicyclo[2.2.1]heptane-2-carboxylate. In the acyloxylation reaction, unusual endo -selectivity was observed owing to 7-azabicyclo[2.2.1]heptane skeleton.