Highly diastereoselective synthesis of 2-azabicyclo[2.2.1]hept-5-ene derivatives: Bronsted acid catalyzed aza-Diels–Alder reaction between cyclopentadiene and imino-acetates with two chiral auxiliaries
2011; Elsevier BV; Volume: 67; Issue: 37 Linguagem: Inglês
10.1016/j.tet.2011.06.097
ISSN1464-5416
AutoresXerardo García‐Mera, José E. Rodríguez‐Borges, M.L.C. Vale, M. José Alves,
Tópico(s)Oxidative Organic Chemistry Reactions
ResumoThe cycloaddition between protonated glyoxylate imines possessing two chiral auxiliaries, N-(S)-or N-(R)-1-phenylethyl and (-)-8-phenylmenthyl or (+)-8phenylneomenthyl, and cyclopentadiene is described.The absolute configuration of all adducts formed was unequivocally assigned through NMR, specific optical rotation and X-ray data of appropriated derivatives.Experimental results confirm the highly exoselectivity for these aza-Diels-Alder reactions, single adducts being obtained from combinations of (8PM)-(R-PEA) and (8PNM)-(S-PEA).
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