A new synthesis of pyrrolidines by way of an enantioselective Mannich/diastereoselective hydroamination reaction sequence
| Autor: | James L. Leighton, Jenny M. Baxter Vu |
|---|---|
| Rok vydání: | 2011 |
| Předmět: |
Pyrrolidines
Silylation Molecular Structure Organic Chemistry Enantioselective synthesis Ketene Stereoisomerism Biochemistry chemistry.chemical_compound chemistry Reaction sequence Cyclization Organic chemistry Lewis acids and bases Hydroamination Physical and Theoretical Chemistry Amination Hydrogen |
| Zdroj: | Organic letters. 13(15) |
| ISSN: | 1523-7052 |
| Popis: | A new two-step synthesis of highly substituted pyrrolidines has been developed. Chiral silane Lewis acid promoted enantioselective Mannich reactions of silyl ketene imines with acylhydrazones may be used to access bishomoallylic benzoic hydrazides that in turn may be cyclized to pyrrolidines by way of the thermal hydroamination reaction reported recently by Beauchemin. Importantly, excellent diastereoselectivity may be realized in the hydroamination reactions. |
| Databáze: | OpenAIRE |
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