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Synthesis of Enantiopure Highly Functionalized Pyrrolizines and Indolizines from Natural α‐Amino Acids: An Experimental and Theoretical Investigation
Author(s) -
Borsini Elena,
Broggini Gianluigi,
Contini Alessandro,
Zecchi Gaetano
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200701217
Subject(s) - enantiopure drug , chemistry , cycloaddition , nitrone , regioselectivity , intramolecular force , stereochemistry , hydroxymethyl , pyrrole , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis
Variously substituted enantiopure 2‐benzylamino‐1‐hydroxymethyl‐2,3‐dihydro‐1 H ‐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)