Investigation of the reaction between amino acids or amino acid esters and 9-formylfluorene and its equivalents. Possible utility of the derived enamines as amino …

LA Carpino, HG Chao, JH Tien

Index: Carpino, Louis A.; Chao, Hann Guang; Tien, Jien-Heh Journal of Organic Chemistry, 1989 ,  vol. 54,  # 18  p. 4302 - 4313

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Citation Number: 14

Abstract

Treatment of 9-(hydroxymethylene) fluorene/g-formylfluorene (storable as the hemiacetal with methanol, 7) with amino acids and amino acid esters yields the corresponding enamines 8, which may be considered to be hydrocarbon analogues of N-formyl amino acid derivatives. Attempted coupling of the free acids 8 (R'= H) with amino acid esters failed, suggesting insufficient reduction in basicity of the amino group due to the enamine ...