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Synthesis of Functionalized Novel α ‐Amino‐ β ‐alkoxyphosphonates through Regioselective Ring Opening of Aziridine‐2‐phosphonates
Author(s) -
PolatCakir Sidika,
Beksultanova Nurzhan,
Dogan Özdemir
Publication year - 2019
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201900199
Subject(s) - aziridine , chemistry , regioselectivity , yield (engineering) , ring (chemistry) , amino acid , allylic rearrangement , organic synthesis , organic chemistry , combinatorial chemistry , catalysis , biochemistry , materials science , metallurgy
Abstract Aziridines are highly useful compounds as building blocks for the synthesis of important organic compounds. Amino acid synthesis by aziridine ring opening reaction is a good example to the use of aziridines. Although this reaction is studied by many groups, the synthesis of amino phosphonic acids is less explored. In this study, we have carried out the ring opening reaction of aziridinyl phosphonates with a variety of alcohols including the more functional propargylic and allylic alcohols. These reactions provided functionalized α ‐amino‐ β ‐alkoxyphosphonates in 40–91 % yield.