Stereoselective allylation of α-hydroxy aldimines and its application to the formal synthesis of (−)-β-conhydrine
| Autor: | Won-Hun Ham, In-Soo Myeong, Jin-Seok Kim, Changyoung Jung, Yong-Taek Lee, Sanghyun Lee |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Aldimine Conhydrine 010405 organic chemistry Stereochemistry Organic Chemistry Alcohol 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Stereocenter chemistry.chemical_compound Formal synthesis chemistry Drug Discovery Stereoselectivity Lewis acids and bases Vicinal |
| Zdroj: | Tetrahedron. 74:506-511 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2017.12.024 |
| Popis: | Stereoselective allylation of N-p-methoxyphenyl (PMP)-substituted α-hydroxy aldimines is described. Several Lewis acids (BF3·OEt2, SnCl4, TiCl4, ZnCl2, and MgBr2·OEt2) were employed to mediate the allylation reactions. The addition of the allyl group generates a new stereocenter and affords the syn vicinal amino alcohol. Formal synthesis of (−)-β-conhydrine (1) was accomplished via syn-selective allyl addition to N-PMP-substituted α-hydroxy aldimine. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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