Diastereoselective alkylations of oxazolidinone glycolates: A useful extension of the Evans asymmetric alkylation

Organic Letters

Volumn 2, Issue 14, 2000, Pages 2165-2167

  Crimmins, Michael T ^a   Emmitte, Kyle A ^a   Katz, Jason D ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOLIC ACID DERIVATIVE; OXAZOLE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMISTRY; HYDROXYLATION; STEREOISOMERISM; SYNTHESIS;

ALKYLATION; GLYCOLATES; HYDROXYLATION; OXAZOLES; STEREOISOMERISM;

EID: 0034644037     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006091m     Document Type: Article

References (33)

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26. Typical procedure for the alkylaiton of oxazolidinone glycolates: A solution of 5.0 mL (3 mmol) of sodium bistrimethylsilylamide (0.6 M in toluene) in 10 mL of THF was cooled to -78°C. A solution of oxazolidinone glycolate (2 mmol) in 5 mL of THF was added dropwise over 5 min. The solution was stirred at -78°C for 30 min. A solution of allyl iodide (10 mmol) in 5 mL of THF was added dropwise. The solution was stirred at -78°C for 5 min and allowed to warm to -40 to -45°C at which temperature it was stirred for 1-3 h. The reaction was monitored by TLC. After the reaction was deemed to be complete, saturated aqueous ammonium chloride was added and the mixture was warmed to room temperature. The mixture was partitioned between 1:1 ethyl acetate/hexanes and water. The organic layer was washed with saturated sodium chloride solution, dried, and concentrated. The residue was purified by flash chromatography to provide the pure alkylation product. Yields are for isolated, chromatographically purified products which were homogeneous by TLC and NMR.
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