Preparation of optically active 2-aminoalkylphosphinic and phosphonic acids
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Synopsis of recent synthetic methods and biological applications of phosphinic acid derivatives
2020, TetrahedronCitation Excerpt :Secondly, it will provide synopsis of the current state of the development that has been made in the biological application and drug with selected examples. An elegant, efficient one-pot synthesis of optically active N-tosylaminophosphinic acid 2 was accomplished by treatment of aziridine 1 with sodium ethyl methylphosphinate in THF at room temperature (Scheme 1) [53]. In a similar manner, Vederas et al. [54] disclosed the reaction of dimethyl phenyl phosphonite with optically active N-Boc-3-amino-2-oxetanone 3 led to the formation of 4 due to methyl migration from the phosphonite onto the carboxylate caused in ring opening [55] (Scheme 2).
Nickel-catalyzed regio- and stereoselective hydrophosphinylation of internal ynamides with H-phosphinates
2018, TetrahedronCitation Excerpt :The requisite ynamides 2b and 2d were prepared by alkynylation of carbamates 1b and 1d according to Danheiser's method [18] and Hsung's method [19], respectively (Scheme 2). Other compounds 2a [15], 2c [20], 2e, g, h, j [21], 2f [22], 2i [23], and 2k [24] were prepared according to literature procedures. In order to achieve the desired transformation, internal ynamide 2a and H-phosphinate 3a were employed as model substrates to optimize the reaction parameters, in particular the transition metal catalysts (Table 1).
Asymmetric catalysis as a method for the synthesis of chiral organophosphorus compounds
2014, Tetrahedron AsymmetryCitation Excerpt :Enzyme catalysis (biocatalysis) has found an increasing number of applications in organic chemistry including the synthesis of optically active compounds.75 Living microorganisms that excrete enzymes directly into the reaction medium can be used to carry out biocatalytic reactions in which racemic or prochiral substrates are transformed into enantiopure compounds.75–98 The biosynthesis of phosphorus compounds was carried out using various yeasts, microscopic fungi, and bacteria that are sources of biocatalysts which can be isolated and used separately.
Synthesis and biological evaluation of reversible inhibitors of IdeS, a bacterial cysteine protease and virulence determinant
2009, Bioorganic and Medicinal ChemistryVersatile use of acid-catalyzed ring-opening of β-aziridinyl-α,β-enoates to stereoselective synthesis of peptidomimetics
2007, TetrahedronCitation Excerpt :Ring-opening reactions of N-activated aziridines have been widely used for the synthesis of various biological compounds such as β-lactams, alkaloids, dipeptide isosteres and sphingosines. Ample precedents, in which nucleophilic reagents, including acids such as HCl, AcOH, TFA and TsOH, attack either of the two carbon atoms of simple aziridines to afford the corresponding ring-opened products, have been documented to date.1 The regiospecific ring-opening reactions of N-2,4,6-trimethylphenylsulfonyl (Mts)-protected (and activated) aziridines possessing α,β-unsaturated esters by strong acids, such as methanesulfonic acid (MSA), TFA or HCl (Scheme 1) have been reported by us.2