Tandem overman rearrangement and intramolecular amidomercuration reactions. stereocontrolled synthesis of cis- and trans-2,6-dialkylpiperidines.
[reaction: see text] Hg(II)-mediated tandem Overman rearrangement and intramolecular amidomercuration reactions were proven to provide a convenient tool for the stereoselective synthesis of cis- and trans-2,6-disubstituted piperidines. Thus, upon treatment with Hg(OTFA)(2) in THF, the trichloroacetimidate 1 directly transformed into the 2,6-dialkyl piperidine 2 with almost exclusive trans selectivity. The amiodomercuration reaction of the carbamate 7 by Hg(OTFA)(2) in nitromethane showed an excellent cis selectivity. Also reported is the stereoselective synthesis of solenopsin A and isosolenopsin A.
Department of Chemistry, The University of Texas at San Antonio, 6900 N. Loop 1604 West, San Antonio, Texas 78249, USA.
Om V
OV
Singh
Hyunsoo
H
Han
D000470:Alkaloids / Q000138:chemical synthesis*; D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D007202:Indicators and Reagents; D008628:Mercury / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D000475:Alkenes; D007202:Indicators and Reagents; D010880:Piperidines; C002351:Solenopsin A; D008628:Mercury