Stereoselective Allylation of Linear and Chiral β-Amino-α-Hydroxy Aldehydes: Total Syntheses of Tetraacetyl d-lyxo-, d-ribo-, and d-arabino-Phytosphingosines
| Autor: | In-Soo Myeong, Jin-Seok Kim, Changyoung Jung, Yong-Taek Lee, Muyng-Gyu Park, Hwan-Hee Jeon, Won-Hun Ham |
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| Rok vydání: | 2018 |
| Předmět: |
0301 basic medicine
chemistry.chemical_classification 030102 biochemistry & molecular biology 010405 organic chemistry Stereochemistry Organic Chemistry Substrate (chemistry) 01 natural sciences Aldehyde Catalysis 0104 chemical sciences 03 medical and health sciences chemistry Chelation Stereoselectivity Lewis acids and bases |
| Zdroj: | Synthesis. 50:2058-2066 |
| ISSN: | 1437-210X 0039-7881 |
| DOI: | 10.1055/s-0037-1609343 |
| Popis: | The stereoselective allylations of β-amino-α-hydroxy aldehydes are described. Several Lewis acids (BF3·OEt2, SnCl4, TiCl4, ZnCl2, and MgBr2·OEt2) were utilized in the allylations. The allylation of anti-β-NHCbz-α-OTBS substrate mediated by SnCl4 afforded the syn-selective product, while its allylation mediated by BF3·OEt2 afforded the anti-selective product. The allylation of syn-β-NHCbz-α-OTBS mediated by SnCl4 afforded the anti-selective product. The mechanism involves the chelation between the amido group and aldehyde oxygen by SnCl4, and the Felkin–Anh model by BF3·OEt2. The resulting allylation products were used for the total syntheses of tetraacetyl d-lyxo-, d-ribo-, and d-arabino-phytosphingosines. |
| Databáze: | OpenAIRE |
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