Phosphite Oxidation and the Preparation of Five-Membered Cyclic Phosphorylating Reagents Via the Phosphites |
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| Authors: | I Ugi P Jacob B Landgraf C Ruppf P Lemmen U Verfürth |
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| Institution: | Organisch-Chemisches Institut, Technische Universitat Miinchen , Lichtenbergstrafle 4, D-8046, Garching, FRG |
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| Abstract: | Abstract The oxaziridines oxidize smoothly phosphites and other P(III) compounds; with chiral oxaziridines the oxidation is enantioselective. Some cyclic phosphorylating reagents are synthetized via the phosphites. The five-membered cyclic phosphorylating reagents 1 show some promise for the development of automated solid phase syntheses of DNA segments by direct phosphorylation. With 0,N,S as P-connected ring atoms and at least one sp2- carbon as a ring member, the computer program IGOR1,2 generated 278 constitutional formulas 1. Since certain thiol phosphates have favorable cleavage properties3, la and lb are particularly interesting candidates to be synthetized4 and to be tested as five-membered cyclic phosphorylating reagents for oligonucleotide syntheses. |
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