[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.
Pyridine derivatives R 0380 A [3 + 3] Annelation Approach toTetrahydropyridines. -The stepwise protocol proceeds via addition of the Buechi-Grignard to aziridines. The method is applied to the synthesis of the alkaloid (-)-dihydropinidine (XIII). -(PATTENDEN, L. C.; WYBROW, R. A. J.; SMITH, S. A.; HARRITY*, J. P. A.; Org. Lett. 8 (2006) 14, 3089-3091; Dep. Chem., Univ. Sheffield, Sheffield S3 7HF, UK; Eng.) -R. Steudel 46-182
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.