Stereoselective Synthesis of 2-Amino Alcohols by Use of an Isocyanide as an Aminomethylene Equivalent

Article abstract of DOI:10.1021/jo00076a042

Preparation of an isocyanide having removable N-substituent and its application to the stereoselective synthesis of 2-amino alcohols are described. 4-(tert-Butyldimethylsiloxy)-2,6-xylyl isocyanide was prepared from commercially available 3,5-xylenol.The isocyanide underwent a samarium iodide-mediated coupling reaction with organic halides and carbonyl compounds.Reduction of the reaction mixture with NaBH4 selectively afforded anti 2-(arylamino) alcohols, which were then deprotected to the corresponding 2-(primary amino) alcohols via desilylation with TBAF followed by oxidation with DDQ.A ceramide was successfully synthesized by use of the present stereoselective synthetic method for 2-amino alcohols, demonstrating a new synthetic utility of the isocyanide as an aminomethylene equivalent.