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Experimental and computational study of the ring opening of tricyclic oxanorbornenes to polyhydro isoindole phosphonates

Tijdschriftbijdrage - Tijdschriftartikel

Phosphonylated azaheterocycles are an important class of compounds with high biological potential as conformationally restricted bioisosteres of amino acids. Therefore, it is of interest to synthesize conformationally constrained amino phosphonates. We wanted to investigate possible routes via ring opening of alpha-amino phosphonates with an oxanorbornene skeleton, as these can be synthesized with high stereoselectivity. This was achieved using different Lewis acids, leading to a range of products. The reaction with TiCl4 and FeCl3 was modelled at a DFT level of theory to get insight in the pathways towards the corresponding products. To ease the work up, the Fe(III) catalyst was coated on montmorillonite clay, but this accelerated aromatization after ring opening. Quenching the FeCl3 catalyzed reaction mixture on celite caused complete aromatization.
Tijdschrift: Organic & Biomolecular Chemistry
ISSN: 1477-0520
Issue: 16
Volume: 8
Pagina's: 3644 - 3654
Jaar van publicatie:2010
Trefwoorden:Organische en medische scheikunde