Synthesis of Enantiopure Highly Functionalized Pyrrolizines and Indolizines from Natural α-Amino Acids: An Experimental and Theoretical Investigation
✍ Scribed by Elena Borsini; Gianluigi Broggini; Alessandro Contini; Gaetano Zecchi
- Publisher
- John Wiley and Sons
- Year
- 2008
- Tongue
- English
- Weight
- 342 KB
- Volume
- 2008
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Abstract
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)