Aza-mannich Reaction Of Tert-butyl Sulfonamide-induced

Mannich's methodology for the construction ofβ-amino carbonyls has been a fundamental tool of the synthetic organic chemistry for decades. Originally limited to dialkylamino methylenation, the application of Mannich reaction has been expanded much further in recent years to a wide variety of monosubstituted amines, amine equivalents and amides. In addition, a variety of Aza-Mannich and Mannich-Michael methodologies have emerged. Meanwhile, the role of Aza-Mannich methodology becomes more and more important in asymmertric synthesis.In this thesis, we report a self-condensation of tert-butanesulfinimine 5 in the presence of tetrabutylammonium fluoride affords unsaturated sulfinimines 8 in moderate to high yields with high geometric selectivities. The synthesizedα,β-unsaturated sulfinimines 8 was demonstrated to be a versatile intermediate for the syntheses of enal 4 and chiral allyl amine 14.