Access to trans-3,4-Dihydroxy-2-alkylpyrrolidines and Piperidines by Use of Stereodefined Cyclic N,O-Acetals as a Diversity-generating Element
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- Title
- Access to trans-3,4-Dihydroxy-2-alkylpyrrolidines and Piperidines by Use of Stereodefined Cyclic N,O-Acetals as a Diversity-generating Element
- Authors
- Kang, S; Kim, DG; Rhee, YH
- Date Issued
- 2014-12-01
- Publisher
- Wiley-VCH
- Abstract
- A highly efficient and stereoselective synthetic pathway towards trans-3,4-dihydroxy-2-alkylpyrrolidines and piperidines is described. The nature of the protecting groups on the hydroxyl moieties played a crucial role on the trans selectivity. By using this method, a concise total synthesis of (-)-2-epilentiginosine has been achieved.
- Keywords
- diastereoselectivity; enantioselectivity; heterocycles; natural products; synthetic methods; N-ACYLIMINIUM IONS; OXOCARBENIUM IONS; EFFICIENT SYNTHESIS; DERIVATIVES; INDOLIZIDINES; NUCLEOPHILES; ALLYLATION; INHIBITORS; CHEMISTRY; AMINES
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/13797
- DOI
- 10.1002/CHEM.201404659
- ISSN
- 0947-6539
- Article Type
- Article
- Citation
- CHEMISTRY-A EUROPEAN JOURNAL, vol. 20, no. 49, page. 16391 - 16396, 2014-12-01
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