title: Rapid synthesis of highly functionalised α-amino amides and medium ring lactones using multicomponent reactions of amino alcohols and isocyanides.
abstract: Four-component reactions between amino alcohols, aldehydes, isocyanides and thiols proceed rapidly under microwave or conventional heating at 60 °C in methanol. The reaction is successful with a wide range of components and gives access to potentially drug-like products containing amine, amide and thioether functionality in moderate to excellent yield. The reaction conditions are also applicable to the synthesis of a range of 8-10 membered medium ring lactones via three-component reactions of amino alcohols, isocyanides and acid-aldehydes. Incorporation of L-prolinol as the amino alcohol component in each case gives access to multicomponent products with moderate to high diastereoselectivity.
authors.affiliation: Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon St., London, UK WC1H 0AJ.
authors.forename: Martin
authors.initials: M
authors.lastname: Bachman
authors.forename: Sam E
authors.initials: SE
authors.lastname: Mann
authors.forename: Tom D
authors.initials: TD
authors.lastname: Sheppard
mesh_terms: D000577:Amides / Q000138:chemical synthesis*; D000605:Amino Alcohols / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D013058:Mass Spectrometry
chemical_list: D000577:Amides; D000605:Amino Alcohols; D003486:Cyanides