Tetrahedron

Highly diastereoselective synthesis of 2-azabicyclo [2.2. 1] hept-5-ene derivatives: Bronsted acid catalyzed aza-Diels–Alder reaction between cyclopentadiene and …

X García-Mera, JE Rodríguez-Borges, MLC Vale…

Index: Garcia-Mera, Xerardo; Rodriguez-Borges, Jose E.; Vale, M. Luisa C.; Alves, Maria J. Tetrahedron, 2011 , vol. 67, # 37 p. 7162 - 7172

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Citation Number: 13

Abstract

The cycloaddition between protonated glyoxylate imines possessing two chiral auxiliaries, N- (S)-or N-(R)-1-phenylethyl and (−)-8-phenylmenthyl or (+)-8-phenylneomenthyl, 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 exo-selectivity for these ...