A [3 + 3] annelation approach to tetrahydropyridines.
[reaction: see text] A stepwise [3+3] annelation sequence to tetrahydropyridines via addition of the Büchi Grignard to aziridines has been developed. These intermediates can be further functionalized with good regio- and stereocontrol and this methodology has been employed in the stereoselective formal synthesis of (-)-dihydropinidine.
Pattenden
Lisa C
LC
Department of Chemistry, University of Sheffield, Brook Hill, UK.
Wybrow
Robert A J
RA
Smith
Stephen A
SA
Harrity
Joseph P A
JP
D002384:Catalysis; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis*; D011725:Pyridines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D010880:Piperidines; D011725:Pyridines; C409726:dihydropinidine