Silylmethyl-substituted aziridine and azetidine as masked 1,3- and 1,4-dipoles for formal [3 + 2] and [4 + 2] cycloaddition reactions.
2-tert-Butyldiphenylsilylmethyl-substituted aziridine and the corresponding azetidine reacted efficiently with nitriles and carbonyl substrates to generate imidazoline, oxazolidine, and tetrahydropyrimidine products. The azetidine rearranged efficiently to the pyrrolidine skeleton involving migration of silicon under BF3.Et2O conditions. The tert-butyldiphenylsilylmethyl function, latent to CH2OH group, controlled not only the regioselectivity of aziridine and azetidine cleavage but also the relative stereochemistry of the substituents in the products derived from substituted aziridine.
Yadav
Veejendra K
VK
Department of Chemistry, Indian Institute of Technology, Kanpur 208 016, India. vijendra@iitk.ac.in
Sriramurthy
Vardhineedi
V
D001384:Azetidines / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D003500:Cyclization; D015195:Drug Design; D008697:Methane / Q000737:chemistry*; D008956:Models, Chemical; D008958:Models, Molecular; D009570:Nitriles / Q000737:chemistry; D017646:Organosilicon Compounds / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry
D001384:Azetidines; D001388:Aziridines; D009570:Nitriles; D017646:Organosilicon Compounds; D010080:Oxazoles; D014297:Trimethylsilyl Compounds; C009660:t-butyldimethylsilyl compounds; D008697:Methane; D012825:Silicon