Ozone → [(2R,3R)-2-formyl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

Through a stirring solution of [(2R,3R)-2-styryl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester (27 mg, 0.089 mmol) in methanol (2 mL) at −78° C. was bubbled ozone until the reaction solution was blue in color. Excess triphenylphosine (500 mg) was added, and the reaction was allowed to warm to 23° C. The resulting mixture was concentrated and purified by flash chromatography (SiO2, 7-40% ethyl acetate in hexanes) to give the desired aldehyde (20 mg, 98%) as a pale yellow oil. MS (APCI), m+/z: (M+H)+=230.

Provenance & Evidence