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.
Synthesis of enantiopure highly functionalized pyrrolizines and indolizines from natural alpha-amino acids : an experimental and theoretical investigation / E. Borsini, G. Broggini, A. Contini, G. Zecchi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2008:16(2008 Jun), pp. 2808-2816. [10.1002/ejoc.200701217]
Synthesis of enantiopure highly functionalized pyrrolizines and indolizines from natural alpha-amino acids : an experimental and theoretical investigation
A. ContiniPenultimo
;
2008
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.
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