Squaric Acid Derivatives Prevent the Removal of N-Cbz and N-Fmoc Groups under Catalytic Hydrogenation Reaction

Tetsuro Shinada; Ken-ichi Hayashi; Yasutaka Yoshida; Yasufumi Ohfune

doi:10.1055/s-2000-7655

Synlett 2000; 2000(10): 1506-1508
DOI: 10.1055/s-2000-7655

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Squaric Acid Derivatives Prevent the Removal of N-Cbz and N-Fmoc Groups under Catalytic Hydrogenation Reaction

Tetsuro Shinada^* , Ken-ichi Hayashi, Yasutaka Yoshida, Yasufumi Ohfune

^*Graduate School of Science, Osaka City University, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan; Fax + 81-6-6605-3153; E-mail: ohfune@sci.osaka-cu.ac.jp

Abstract

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Under the catalytic hydrogenation conditions (H₂/Pd-C), squaric acid derivatives 4 and 7 were found to be effective additives for chemoselective reduction of olefins and an alkyne having an N-Cbz or N-Fmoc group where the amino group remained to be protected. Benzyl esters having an N-Cbz or N-Fmoc group were also selectively removed to give the corresponding N-protected carboxylic acids.

hydrogenation - Pd-C - squaric acid derivatives - chemoselectivity - reduction

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