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New and Facile Synthesis of Aminobicyclo[2.2.1]heptane-2-carboxylic Acids
- Authors
- Kim, Taek-Soo; Seo, Seung-Yong; Shin, Dongyun
- Issue Date
- Jun-2015
- Publisher
- GEORG THIEME VERLAG KG
- Keywords
- carbocycles; amino acids; bicyclic compounds; diastereoselectivity; carbonylation
- Citation
- SYNLETT, v.26, no.9, pp.1243 - 1247
- Journal Title
- SYNLETT
- Volume
- 26
- Number
- 9
- Start Page
- 1243
- End Page
- 1247
- ISSN
- 0936-5214
- Abstract
- A facile approach for the stereoselective synthesis of a- and b-2-aminobicyclo[2.2.1]heptane-2-carboxylic acid is described. Substrate-controlled -carboxylation of norbonene monoester delivered the asymmetric diester intermediate with high diastereoselectivity (up to 35:1). Sequential chemoselective ester cleavage, Curtius rearrangement, and hydrolysis gave the a- and b-isomers of 2-aminobicyclo[2.2.1]heptane-2-carboxylic acid, respectively.
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Related Researcher
- Shin, Dong Yun
- Pharmacy (Dept.of Pharmacy)