Journal of Organic Chemistry p. 6766 - 6770 (1993)
Update date:2022-08-04
Topics:
Murakami, Masahiro
Ito, Hajime
Ito, Yoshihiko
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.
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Doi:10.1080/00397919308013801
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