The search for an easily-prepared sparteine surrogate
| Autor: | Vera M. Foley, Gerard P. McGlacken, Rafael Cano |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Silylation
010405 organic chemistry Ligand Parent structure Organic Chemistry Sparteine 010402 general chemistry 01 natural sciences Catalysis Pyrrolidine 0104 chemical sciences Inorganic Chemistry chemistry.chemical_compound chemistry Diamine medicine Organic chemistry Physical and Theoretical Chemistry Enantiomer Selectivity medicine.drug |
| Zdroj: | Tetrahedron: Asymmetry. 27:1160-1167 |
| ISSN: | 0957-4166 |
| DOI: | 10.1016/j.tetasy.2016.09.001 |
| Popis: | (−)-Sparteine has proven itself to be a highly efficient and versatile ligand. However, in recent years it has become difficult to source. In addition the (+)-enantiomer is also not readily available. Here we report a suite of chiral diamines as potential sparteine surrogates. Chiral trans -1,2-diaminocyclohexane is commercially available in both enantiomeric forms and the parent structure can be easily modified. New (and known) chiral diamines have been tested in the asymmetric silylation of N -Boc pyrrolidine, N -Boc piperidine, the α-alkylation of dimethylhydrazones and in the rearrangement of meso -epoxides. While none match the selectivity of the highly evolved natural product, there is certainly potential for this class of diamine ligands to perform in a diverse set of asymmetric transformations. |
| Databáze: | OpenAIRE |
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