Chiral N‐Acylhydrazones: Versatile Imino Acceptors for Asymmetric Amine Synthesis

摘要: Addition to C=N bonds with acyclic stereocontrol offers excellent potential for development of new carbon–carbon bond construction approaches chiral amines. This review features the design and implementation novel N-acylhydrazones as versatile imino acceptors addition radicals nucleophiles. The initial was inspired by goal asymmetric radical acceptors. are prepared from commercially available materials amination 4-alkyl-2-oxazolidinones NH2+ equivalents afford N-(amino)oxazolidinones, followed condensation aldehydes or ketones. These undergo reactions various partners, including radicals, allylsilanes, allylindiums, silyl enol ethers, hydride donors. adducts can be converted amines N–N cleavage. Reliably high stereoselectivity observed in presence Lewis acids. For prototype case, derived (S)-4-benzyl-2-oxazolidinone, two alternative models consistent results. acids capable chelate formation activate through two-point binding nitrogen carbonyl oxygen, exposing si-face addition. On other hand, boron trifluoride activates a monodentate interaction, favoring rotamer which exposes re-face. Applications author’s research program reviewed together results groups. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)