A facile synthesis of new homochiral β-amino alcohols with norbornane framework
✍ Scribed by A.García Martínez; E.Teso Vilar; A.García Fraile; S.de la Moya Cerero; P.Martínez Ruiz; L.R. Subramanian
- Book ID
- 103977481
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- English
- Weight
- 165 KB
- Volume
- 7
- Category
- Article
- ISSN
- 0957-4166
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📜 SIMILAR VOLUMES
The usual pathwsys' for preparing ~-amino alcohols for use in the Tiffeneau-Demjanov reaction involve either preparation of cyanohydrins or t3-nitroalcohols fYan ketones, followed by reduction. Difficulty is encountered with some conjugated and sterically hindered ketones with the initisl addition r
Chiral N-protected p-amino alcohols are easily obtained by NaB& reduction of mixed anhydndes of N-protected a-ammo acids m an organic/aqueous medium. The alcohols obtamed from side chain or main chain reduction of N-protected asparhc acid are converted in good yields into lactones.
Ph "Ellman" "anti-Ellman" Conditions (Table 1) 7a R=TBS 7b R=Bn 8a R=TBS 8b R=Bn CuSO 4 CH 2 Cl 2 Ph + 5 R=TBS (98%) 6 R=Bn (96%) 4 R=TBS R=Bn TETRAHEDRON LETTERS