Nitrosocarbonyl mesitylene intermediate undergoes Ene reaction with the crotyl alcohol affording two regioisomeric adducts in fair yields. The sterically demanding nitrosocarbonyl mesitylene slightly drifts the C2/Markovnikov orientation towards the C3/Anti-Markovnikov pathway affording the 5-hydroxy-isoxazolidine that serves as synthon for the preparation of N,O-nucleoside analogues through the Vorbrüggen protocol. The selectivity of the ene reaction is discussed in the light of C=C double bond polarization and steric effects. The structures of the N,O-nucleosides are attributed and discussed on the basis of spectroscopic observations and X-ray analysis.
N,O-Nucleosides from Ene Reaction of (Nitrosocarbonyl)mesitylene with Crotyl Alcohol: Selectivity, Scope, and Limitations
CAROSSO, SERENA;MEMEO, MISAL GIUSEPPE;BOVIO, BRUNA;QUADRELLI, PAOLO
2017-01-01
Abstract
Nitrosocarbonyl mesitylene intermediate undergoes Ene reaction with the crotyl alcohol affording two regioisomeric adducts in fair yields. The sterically demanding nitrosocarbonyl mesitylene slightly drifts the C2/Markovnikov orientation towards the C3/Anti-Markovnikov pathway affording the 5-hydroxy-isoxazolidine that serves as synthon for the preparation of N,O-nucleoside analogues through the Vorbrüggen protocol. The selectivity of the ene reaction is discussed in the light of C=C double bond polarization and steric effects. The structures of the N,O-nucleosides are attributed and discussed on the basis of spectroscopic observations and X-ray analysis.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
