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Synthesis of protected 1,4-trans-1,5-cis-4,5-diamino-2-cyclopenten-1-ol via stereoselective vinylation of α-amino aldimine
- Authors
- Lee, S.J.[Lee, Seung Jong]; Kim, Y.[Kim, Yun]; Ham, W.-H.[Ham, Won-Hun]; Myeong, I.-S.[Myeong, In-Soo]
- Issue Date
- 11-Jul-2023
- Publisher
- Elsevier Ltd
- Citation
- Tetrahedron Letters, v.124
- Indexed
- SCIE
SCOPUS
- Journal Title
- Tetrahedron Letters
- Volume
- 124
- ISSN
- 0040-4039
- Abstract
- We report the synthesis of diaminocyclitol, protected 1,4-trans-1,5-cis-4,5-diamino-2-cyclopenten-1-ol. The key strategy was stereoselective vinylation of an acyclic chiral α-amino aldimine to construct syn-diamine moiety. The 1,5-cis-amino alcohol moiety was established by stereoselective reduction, and the cyclopentene structure was secured through a ring-closing metathesis reaction. © 2023 Elsevier Ltd
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