Synthesis and use of new phosphineoxy aziridinyl phosphonates (poap) as organocatalysts in asymmetric phosphonylation of aldehydes

İşci, Muhammet
A new phosphineoxy aziridiniyl phosphonates POAP were synthesized as potential organocatalysts and used for silicon based asymmetric Abramov-type phosphonylation of aldehydes with triethyl phosphite. Besides POAP organocatalyst, known chiral phosphineoxy ferrocenyl substituted aziridinyl methanol (POFAM) and aziridinyl phosphonates (AP) were also used for the same reaction. The product α-hydroxy phosphonates were obtained in good yields up to 99% but with poor enantioselectivities. Highest enantioselectivity (%34) was obtained with POAP organocatalyst. Optimization studies were done with different solvents, ligands, aldehydes, and concentrations.


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Citation Formats
M. İşci, “Synthesis and use of new phosphineoxy aziridinyl phosphonates (poap) as organocatalysts in asymmetric phosphonylation of aldehydes,” M.S. - Master of Science, Middle East Technical University, 2012.