[4+2] Cycloaddition of phosphoryl-substituted dienes and dienophiles with a view of preparing aminophosphonic acid derivatives
(2001) Recent Research Developments in Organic Chemistry. vol 5 — ISBN: [9788178950068], published
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- New strategies are proposed for the prepn. of phosphonic acid analogs of amino acids in the context of drug optimization and/or discovery. A general approach towards β-, γ- and δ-aminophosphonic acid derivs. is based on regio- and tereocontrolled [4+2] cycloaddns. of activated phosphoryl-substituted alkenes or alkynes and protected 1-amino-substituted butadiene in the form of succinimide group to give 1-dialkoxyphosphinyl-2-(N-succinimido)-3-cyclohexene-1-carboxylic acid esters (1, endo-, 2, exo-). Selective hydrolysis of the phosphonic group was achieved by reaction of 1, 2 with trimethylsilyl bromide, whereas prolonged reaction with 6N HCl led to deprotection of the amino group also. Further cis- and trans-dihydroxylation and ozonolysis of 1 and 2 led to highly functionalized aminoalkylphosphonic acid derivs. Recent advances in [4+2] cycloaddn. of dienes and phosphonic acid derivs. are discussed.
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Marchand-Brynaert, J., Defacqz, N., & Robiette, R. (2001). [4+2] Cycloaddition of phosphoryl-substituted dienes and dienophiles with a view of preparing aminophosphonic acid derivatives. In Pandalai S.G. (ed.), Recent Research Developments in Organic Chemistry. vol 5. Transworld Research Network. https://hdl.handle.net/2078.5/203028