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DOI: 10.1055/s-0030-1258581
Convenient Procedure for the Indium-Mediated Hydroxymethylation of Active Bromo Compounds: Transformation of Ketones into α-Hydroxymethyl Nitroalkanes
Publication History
Publication Date:
23 September 2010 (online)
Abstract
A very simple, safe and powerful method for the hydroxymethylation of 2-bromoesters and lactones under anhydrous conditions that avoids the use of gaseous formaldehyde is described. Moreover, under these conditions, bromonitroalkanes were converted into the corresponding α-monohydroxymethylated nitroalkanes, which are precursors of the corresponding α-amino acids. Considering the easy transformation of ketones into bromonitroalkanes, this represents a method for the formal synthesis of α-amino acids from ketones.
Key words
hydroxymethylation - indium - esters - nitroalkanes - amino acids
- Supporting Information for this article is available online:
- Supporting Information
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References and Notes
General Procedure: To a suspension of indium powder (0.5 mmol) in THF (1 mL), the 2-bromocompound (0.75 equiv) was added and the mixture was sonicated for 20 min. Paraformaldehyde (0.5 mmol) was then added and sonication was continued for a further 4 h. The reaction mixture was quenched with sat. aq NaHCO3 (10 mL) and extracted with Et2O (3 × 25 mL). The combined organic layers were dried over MgSO4, filtered and the solvent was evaporated in vacuo to obtain pure hydroxymethylated compounds.