α-Amino acid derivatives with a Cα-P bond in organic synthesis

Abstract

α-Amino acid derivatives with a C α -P bond have been used for a wide range of chemical transformations, including synthesis of many kinds of bioactive compounds, e.g. nonproteinogenic α-amino acids, α,β-dehydro-α-amino acids, dehydropeptides, β-lactam antibiotics and glycopeptides. The present review is focused on methods of synthesis of the title compounds, their properties and application in organic synthesis.

1-Aminoalkylphosphonium Derivatives: Smart Synthetic Equivalents of N-Acyliminium-Type Cations, and Maybe Something More: A Review

“…As demonstrated by Mazurkiewicz and Kuźnik, N -acyl-1-triphenylphosphonioglycinate tetrafluoroborates 91 are also convenient starting compounds for the transformation into N -acyl-α-(dialkoxyphosphoryl)glycinates 108 by the Michaelis–Arbuzow-type reaction with trimethylphosphite in the presence of methyltriphenylphosphonium iodide as a catalyst ( Scheme 32 ) [ 89 ]. Among others, α-(dialkoxyphosphoryl)glycinates became the crucial synthetic tool commonly used for the synthesis of many natural products (including β-lactam antibiotics) or α,β-dehydro-α-amino acids by the Wadsworth-Emmons reaction [ 90 , 91 , 92 , 93 , 94 , 95 , 96 ]. As is known, hydrogenation of the latter compounds using chiral catalysts is considered to be one of the most general methods for the enantioselective synthesis of α-amino acids, including non-proteinogenic α-amino acids of diverse biological activities [ 97 , 98 , 99 , 100 ].…”

Theoretical study, synthesis, kinetics and mechanistic investigation of a stable phosphorus ylide in the presence of methyl carbamate as a NH-acid

“…The ylide moiety of these compounds is strongly conjugated with the adjacent carbonyl group and rotation around the partial double bond in (E)-4(a,b) and (Z)-4(a,b) geometrical isomers is slow on the NMR time-scale at ambient temperature (Scheme 1). On the basis of the well-established chemistry of trivalent phosphorus nucleophiles, [3][4][5][6][7] it is reasonable to assume that phosphorus ylide 4 results from the initial addition of triphenylphosphine to the acetylenic esters and subsequent protonation of the 1:1 adduct by the methyl carbamate to form phosphoranes 4. The 2 Scheme 1.…”

“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14] A large number of methods have appeared describing novel syntheses of organophosphorus compounds. 1,2 There are many studies on the reaction between trivalent phosphorus nucleophiles and α, β-unsaturated carbonyl compounds in the presence of a proton source such as an alcohol or phenol.…”