Abstract The dianion of N-benzyl-2-propynamide can be generated by the treatment of 4 with two equivalents of LDA at− 65 or ethylmagnesium bromide at− 20. The trilithio species 6 is readily formed using 3 equivalents of LDA. Reaction of 5 with aldehydes or ketones produce hydroxypropynamides 9 in good yields. Silation of 5a with chlorotrimethylsilane produces N-benzyl-3-trimethylsilyl-2-propynamide (13) in high yield. Reduction of 9 ...
