Microwave-assisted synthesis of methyl (1S,2R,4S,5S)-7-aza-5-hydroxybicyclo[2.2.1]heptane-2-carboxylate through unexpected stereoselective substitution reaction |
| |
| Authors: | Satoru OnogiShuhei Higashibayashi Hidehiro Sakurai |
| |
| Institution: | a Department of Functional Molecular Science, School of Physical Sciences, The Graduate University for Advanced Studies, Myodaiji, Okazaki 444-8787, Japan
b Research Center for Molecular Scale Nanoscience, Institute for Molecular Science, Myodaiji, Okazaki 444-8787, Japan |
| |
| Abstract: | Methyl (1S,2R,4S,5R)-7-aza-5-bromo-bicyclo2.2.1]heptane-2-carboxylate was synthesized in high yield in short time from methyl (1R,2S,4R,5R)-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 (1S,2R,4S,5S)-7-aza-5-hydroxy-bicyclo2.2.1]heptane-2-carboxylate. In the acyloxylation reaction, unusual endo-selectivity was observed owing to 7-azabicyclo2.2.1]heptane skeleton. |
| |
| Keywords: | Microwave Azabicyclo[2 2 1]heptane Cycloamination Hydroxylation Endo-selectivity |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
