Stereoselective Addition of Grignard-Derived Organocopper Reagents to N-Acyliminium Ions: Synthesis of Enantiopure 5- and 4,5-Substituted Prolinates
โ Scribed by Collado, Ivan; Ezquerra, Jesus; Pedregal, Concepcion
- Book ID
- 121316097
- Publisher
- American Chemical Society
- Year
- 1995
- Tongue
- English
- Weight
- 634 KB
- Volume
- 60
- Category
- Article
- ISSN
- 0022-3263
No coin nor oath required. For personal study only.
๐ SIMILAR VOLUMES
Reaction of the N-acyliminium ion pmcursor la &??Wedjhm S-proline via anodic methoxykation~ with RCu in the pnsetue of BF,.Et# gives preferentially the trans adducts 2 (trans:ci.s L96:4). Using such a procedure, a general synthetic route to (2R, 5.~~-hans-2,5-d~l~~~l~ines has been developed, as ezmp
Summarv. Addition of RCu, BFs to the electrochemically prepared a-methoxy proline ester 1 has been shown to be highly truns (296 %) selective. This reaction has been developed into an enantioselective synthesis of the ant trail feromone trans-2-butyl-S-heptyylpyrrolidine. Nucleophilic additions to
Methyl magnesium chloride, vinyl magnesium chloride and acetylides were found to add to 4-Otriisopropylphenylsulphonyl (TPS) uridine and thymidine derivatives at the 6-position leading to 6-substituted-3,6-dihydro-4-0-TPS pyrimidine nucleosides. Reaction with phenyl magnesium chloride resulted in ad