Sterically encumbered nitrosocarbonyl mesitylene and anthracene undergo Ene reactions with the 3-methyl-2-buten-1-ol affording the 5-hydroxy-isoxazolidine adducts in fair yields. These heterocycles derive from the anti-Markovnikov orientation of the Ene reaction according to the proposed mechanism. The 5-hydroxy-isoxazolidine acetates are the synthons of choice for the preparation of N,O-nucleoside analogues according to the Vorbrüggen protocol incorporating purine rings.
From the Ene Reaction of Nitrosocarbonyl Intermediates with 3-Methylbut-2-en-1-ol, a New Class of Purine N,O-Nucleoside Analogues
QUADRELLI, PAOLO;MELLA, MARIELLA;BOVIO, BRUNA
2013-01-01
Abstract
Sterically encumbered nitrosocarbonyl mesitylene and anthracene undergo Ene reactions with the 3-methyl-2-buten-1-ol affording the 5-hydroxy-isoxazolidine adducts in fair yields. These heterocycles derive from the anti-Markovnikov orientation of the Ene reaction according to the proposed mechanism. The 5-hydroxy-isoxazolidine acetates are the synthons of choice for the preparation of N,O-nucleoside analogues according to the Vorbrüggen protocol incorporating purine rings.File in questo prodotto:
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