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Rapid synthesis of highly functionalised alpha-amino amides and medium ring lactones using multicomponent reactions of amino alcohols and isocyanides

Bachman, M; Mann, SE; Sheppard, TD; (2012) Rapid synthesis of highly functionalised alpha-amino amides and medium ring lactones using multicomponent reactions of amino alcohols and isocyanides. ORGANIC & BIOMOLECULAR CHEMISTRY , 10 (1) 162 - 170. 10.1039/c1ob06534c. Green open access

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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.

Type:Article
Title:Rapid synthesis of highly functionalised alpha-amino amides and medium ring lactones using multicomponent reactions of amino alcohols and isocyanides
Open access status:An open access version is available from UCL Discovery
DOI:10.1039/c1ob06534c
Publisher version:http://dx.doi.org/10.1039/c1ob06534c
Language:English
Additional information:Bachman, M and Mann, SE and Sheppard, TD (2012) Rapid synthesis of highly functionalised alpha-amino amides and medium ring lactones using multicomponent reactions of amino alcohols and isocyanides. ORGANIC & BIOMOLECULAR CHEMISTRY , 10 (1) 162 - 170. Reproduced by permission of The Royal Society of Chemistry. PubMed ID: 22076284
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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