41003-95-6Relevant academic research and scientific papers
Elucidating the Reaction Pathway of Decarboxylation-Assisted Olefination Catalyzed by a Mononuclear Non-Heme Iron Enzyme
Yu, Cheng-Ping,Tang, Yijie,Cha, Lide,Milikisiyants, Sergey,Smirnova, Tatyana I.,Smirnov, Alex I.,Guo, Yisong,Chang, Wei-Chen
supporting information, p. 15190 - 15193 (2018/11/23)
Installation of olefins into molecules is a key transformation in organic synthesis. The recently discovered decarboxylation-assisted olefination in the biosynthesis of rhabduscin by a mononuclear non-heme iron enzyme (P.IsnB) represents a novel approach in olefin construction. This method is commonly employed in natural product biosynthesis. Herein, we demonstrate that a ferryl intermediate is used for C-H activation at the benzylic position of the substrate. We further establish that P.IsnB reactivity can be switched from olefination to hydroxylation using electron-withdrawing groups appended on the phenyl moiety of the analogues. These experimental observations imply that a pathway involving an initial C-H activation followed by a benzylic carbocation species or by electron transfer coupled β-scission is likely utilized to complete C=C bond formation.
A Facile Conversion of Aminoalkanephosphonic Acids into Their Diethyl Esters. The Use of Unblocked Aminoalkanephosphonic Acids in Phosphono Peptide Synthesis
Kafarski, Pawel,Lejczak, Barbara
, p. 307 - 310 (2007/10/02)
A simple and efficient, two-step procedure for the preparation of diethyl aminoalkylphosphonates from aminoalkylphosphonic acids is reported.The obtained esters are useful as substrates in phosphono peptide synthesis.
Method for preparation of N-phosphonomethylglycine
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, (2008/06/13)
A method for the production of N-phosphonomethylglycine is disclosed which comprises the steps of: (a) reacting formaldehyde with formamide at a pH of 9-10 to form N-(hydroxymethyl)formamide, (b) reacting N-(hydroxymethylformamide with triethylphosphite to form diethyl, N-(formyl)aminomethylphosphonate, (c) reacting diethyl, N-(formyl)aminomethylphosphonate with methylchloroacetate to form N-(diethylphosphonomethyl), N-(formyl)glycinemethyl ester, and (d) reacting N-(diethylphosphonomethyl), N-(formyl)glycinemethyl ester with hydrochloric acid to form N-phosphonomethylglycine.
