104713-86-2Relevant academic research and scientific papers
Stereocontrolled preparation of cis- and trans-2,6-dialkylpiperidines via diastereoselective reaction of 1-aza-4-oxabicyclo[4.3.0]nonane derivatives with Grignard reagents
Poerwono, Hadi,Higashiyama, Kimio,Yamauchi, Takayasu,Kubo, Hajime,Ohmiya, Shigeru,Takahashi, Hiroshi
, p. 13955 - 13970 (2007/10/03)
We report here the syntheses of cis- and trans-2,6-disubstituted piperidines using chiral 1-aza-4-oxabicyclo[4.3.0]nonane synthon 1, which shows high reactivity toward nucleophilic attack at its C-5 position. Bicyclic compounds resembling synthon 1 were transformed to cis- and trans- 2,6-disubstituted piperidine derivatives via reactions with various Grignard reagents in a stereospecific manner. Using this methodology, (+)-solenopsin A (2b) and both enantiomers of isosolenopsin A (3a and 3b) were synthesized in an enantioselective manner from a single enantiomeric source.
