Synthesis of chiral spirocyclo-quaternary ammonium salts from L-proline and their application as phase-transfer catalysts in asymmetric alkylation

doi:10.5246/jcps.2011.01.003

Abstract

CLC Number:

R916

Supporting:

Na Wang, Song-Wen Lin, Qing Yang, Qi Sun^*, Run-Tao Li^*. Synthesis of chiral spirocyclo-quaternary ammonium salts from L-proline and their application as phase-transfer catalysts in asymmetric alkylation [J]. , DOI: 10.5246/jcps.2011.01.003.

References

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[10] Typical experimental procedure: To a test tube containing 9 (0.30 g, 1 mmol), benzyl bromide (0.19 g, 1.1 mmol) and base solution (5 mL) in 15 mL toluene, catalyst 7 was added at 0 °C. After stirring for 48 h at 0 °C, the reaction was quenched with water and extracted with Et2O (3×10 mL). The combined organic layers were washed with water and dried over Na2SO4. The solvents were removed in vacuo and subsequent flash column chromatography with petrolem-ethyl acetate (80:1, v/v), then petrolem-ethyl acetate (40:1, v/v), gave the desired product 10. The enantiomeric excess was determined by HPLC [Daicel Chiralcel OD, hexane: i-PrOH = 97: 3, flow rate: 1 mL/min (254 nm), retention times: 4.24 min (R, major) and 4.98 min (S, minor)].
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