A Convenient Oxazole C-2 Protecting Group: The Synthesis of 4- and 5-Substituted Oxazoles via Metalation of 2-Triisopropylsilyloxazoles

Metalation of oxazoles at the 4 and 5 position was achieved after regioselective C-2 silyl protection. Removal of the protecting group was then accomplished under mild conditions allowing for a straightforward preparation of C-5 monosubstituted and C-4,5 disubstituted oxazoles. The first practical C-2 protecting group of oxazoles has been demonstrated

A Convenient Oxazole C-2 Protecting Group: The Synthesis of 4- and 5-Substituted Oxazoles via Metalation of 2-Triisopropylsilyloxazoles

Metalation of oxazoles at the 4 and 5 position was achieved after regioselective C-2 silyl protection. Removal of the protecting group was then accomplished under mild conditions allowing for a straightforward preparation of C-5 monosubstituted and C-4,5 disubstituted oxazoles. The first practical C-2 protecting group of oxazoles has been demonstrated

Methoxymethylation of Alcohols, Phenols, and Avermectin Aglycones Using MOM-2-pyridylsulfide

Methoxymethyl-2-pyridylsulfide (MOM-ON) is an effective methoxymethylating reagent when used in conjunction with AgOTf, NaOAc, and THF. A wide range of MOM ethers are produced from corresponding phenols and alcohols, including tertiary and allylic alcohols, in good yields and under mild, neutral conditions. This method is also effective for the methoxymethylation of avermectin aglycones