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. 10.1039/c1ob06534c.
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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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