Solid-Phase Synthesis: Intramolecular Azomethine Ylide Cycloaddition (→Proline) and Carbanilide Cyclization (→Hydantoin) Reactions

Citations Over TimeTop 12% of 1998 papers

Abstract

An efficient, diastereoselective route to 2,5,6,7-tetrasubstituted-1H-pyrrolo[1,2-c]imidazoles has been developed using solid-phase intramolecular azomethine ylide cycloaddition and carbanilide cyclization chemistries. To successfully execute this eight-step protocol in the solid phase, it was necessary to insert a spacer moiety between the resin and glycinate functional group. Experiments addressing the stereoselectivity of the 1,3-dipolar cycloaddition step as well as the cyclative release step are also presented.

Related Papers

• → An Efficient Synthesis of Stable Phosphorus Ylides Derived from Hydantoin and 5,5-dialkylhydantoins(2002)27 cited
• → Microwave-assisted solid-phase synthesis of hydantoin derivatives(2007)48 cited
• → Diastereoselective synthesis of pyrrolidines via 1,3-dipolar cycloaddition of a chiral azomethine ylide(2009)32 cited
• → 1,3-Dipolar cycloaddition between acetylenic dipolarophiles and sydnone-N-ylides as bis(1,3-dipoles)(2015)16 cited
• → Pyrrolidines by 1,3-Dipolar Cycloaddition of Conjugated Azomethine Ylides(1995)20 cited