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Synlett

Volumn , Issue 4, 2007, Pages 538-542

Enantioselective α-oxytosylation of ketones catalysed by iodoarenes

(6) Richardson, Robert D a Page, T Keri a Altermann, Sabine a Paradine, Shauna M b French, Andrew N b Wirth, Thomas a

a CARDIFF UNIVERSITY (United Kingdom)

b ALBION COLLEGE (United States)

Author keywords

Hypervalent iodine reagents; Organocatalysis; Oxidation; Stereoselective synthesis

Indexed keywords

IODOARENE DERIVATIVE; KETONE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY;

EID: 33947259792 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-967960 Document Type: Article

Times cited : (129)

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- After seeing results of Y. Kita (Dohi, T.; Maruyama, A.; Minamitsuji, Y.; Takenaga, N.; Kita, Y. Chem. Commun. 2007, DOI: 10.1039/b616510a, in press) in which 2,2,2-trifluoroethanol can be used as solvent to increase the rate of oxidation of 4-iodotoluene by mCPBA, we applied to the iodobenzene-catalysed oxytosylation of propiophenone but this gave no increase in reaction rate.

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- Representative Experimental Procedure A solution of propiophenone (1, 67 mg, 0.5 mmol) in MeCN (1 mL) was added to a solution of iodoarene 5 (15 mg, 0.05 mmol) TsOH·H2O (285 mg, 1.5 mmol) and mCPBA (366 mg, 77% wet with H2O, 1.5 mmol) in MeCN (2 mL) at r.t. The resulting solution was stirred at r.t. for 60 h then quenched by addition of sat. aq Na2S2O3 (5 mL) and sat. aq Na 2CO3 (5 mL, The mixture was extracted with EtOAc (3 x 5 mL, the combined organic layers were washed with brine (10 mL, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (SiO2, 80:20 hexane-EtOAc) to yield tosylate 3 119 mg, 0.39 mmol, 78, as a white powder. The ee was determined by HPLC on the crude and purified products: Chiracel OB-H column, 40:60 hexane-2-PrOH, 0.5 mL·min-1
- R = 18.1 min (R), 21.6 min (S).

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