10.1002/adsc.201901356
Advanced Synthesis & Catalysis
1
mixture was determined by H-NMR with anisole as the
internal standard.
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General Procedure for the α-Tosyloxylation of Carbonyl
Compounds 8 with 1 mol% Catalyst 10e.
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To a stirred mixture of mCPBA (85%, 306 mg, 1.50 mmol,
1.5 equiv), KOTs (105 mg, 0.500 mmol, 0.5 equiv) and
TsOH•H2O (162 mg, 0.850 mmol, 0.85 equiv) in MeCN
(5 mL, 0.2 M) is added the catalyst 10e (3.5 mg,
0.010 mmol, 1 mol%) followed by the corresponding
carbonyl compound 8 (1.00 mmol) and the mixture was
stirred at 80 °C for 6 h. Then water (10 mL) and sat.
Na2S2O3-solution (2 mL) was added and the mixture was
extracted with EtOAc (3 x 15 mL). The combined organic
phases were washed with sat. NaHCO3-solution
(2 x 20 mL), dried over Na2SO4, filtered and concentrated
under reduced pressure. The residue was purified via
column chromatography on silica gel (cyclohexane/EtOAc)
to give the corresponding product 9.
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Acknowledgements
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Funding by the Fonds der Chemischen Industrie (PhD
scholarship to AB) is gratefully acknowledged.
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