E. Borsini, G. Broggini, A. Contini
Jun 1, 2008
Citations
0
Influential Citations
19
Citations
Journal
European Journal of Organic Chemistry
Abstract
Variously substituted enantiopure 2-benzylamino-1-hydroxymethyl-2,3-dihydro-1H-pyrrolizines and 6-benzylamino-5,6,7,8-tetrahydroindolizin-8-ols have been prepared. The reaction sequence starts from L-α-amino acids and involves an intramolecular cycloaddition of pyrrole-based nitrone intermediates. A theoretical investigation at the HCTH/6-311+G(d,p)//HCTH/6-31+G(d) level of theory was performed with the aim of rationalizing the effects of substituents on the regiochemistry of the cycloaddition reaction.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)