The Journal of Organic Chemistry

Stereoselective synthesis of 2-amino alcohols by use of an isocyanide as an aminomethylene equivalent

M Murakami, H Ito, Y Ito

Index: Murakami, Masahiro; Ito, Hajime; Ito, Yoshihiko Journal of Organic Chemistry, 1993 , vol. 58, # 24 p. 6766 - 6770

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Citation Number: 25

Abstract

Preparation of an isocyanide having a 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 iodidemediated coupling reaction with organic halides and carbonyl compounds. Reduction of the reaction mixture with NaBH4 selectively afforded anti 2-( ...