Asymmetric synthesis of 2H-aziridine phosphonates, and α- or β-aminophosphonates from enantiomerically enriched 2H-azirines

Applications of Chiral Three-membered Rings for Total Synthesis: A Review

“…The scope of this methodology was extended to the synthesis of enantioenriched 2H-azirines derived from phosphonates albeit with lower enantioselectivities ranging from 20 to 52% ee along with high yields (85-95%) [47]. Later, better enantioselectivities of up to 72% ee were reported by the same authors in the synthesis of chiral 2H-azirine phosphonates 67 performed with the same catalyst in the presence of K 2 CO 3 (Scheme 28) [48]. These three-membered heterocycles constitute important building blocks in the preparation of biologically active compounds of interest in medicinal chemistry including naturally occurring antibiotics.…”

Three‐Membered Heterocycles. Structure and Reactivity

“…Similar cytotoxic activity exhibited by the 16-membered macrolide epothilone A (285), a metabolite of the cellulose-degrading myxobacterium Sorangium cellulosum (Myxococcales), has made it an interesting anti-cancer candidate and subsequently the subject of active investigation from both a synthetic organic and chemical biology standpoint [325,326]. Also of marine origin is the bromotyrosine-derived dimeric spiroisoxazoline ( þ )-calafianin (286), which is found in methylene chloride extracts of the Mexican sponge Aplysina gerardogreeni n. sp (Aplysinidae). Members in this class of compounds have demonstrated activity against Mycobacterium tuberculosis [327,328].…”

“…For example, sodium borohydride reacts smoothly in ethanolic medium with azirine 229 to yield the cis-aziridine 235, resulting from the transaddition of hydride [286]. Alternatively, an asymmetric transfer hydrogenation protocol using the chiral aminoalcohol 236 and a ruthenium catalyst can be used to generate enantiomerically enriched aziridines from achiral azirine precursors.…”

Synthesis and HPLC resolution of isomers of novel phosphorus fluorinated 2,4,6-trimethylphenylazo pyridines

“…A combination of fluorinated and diphenylphosphinoyl groups in azo-compounds will hopefully make them very interesting biological active compounds. Since phosphorus substituents regulate important biological functions [1][2][3] and fluorine containing compounds play important role in organic synthesis and in medicinal chemistry [4][5][6][7][8][9][10].…”