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29.6.2.2.5.1 Variation 1: From O/Se Acetals

DOI: 10.1055/sos-SD-129-00001

Fowler, L. S.; Sutherland, A.Science of Synthesis Knowledge Updates, (20103136.

The C—Se bond is weaker than the C—O bond and thus O/Se acetals can be employed as precursors of O/O acetals. This strategy has been used to develop a general approach for the protection of alcohols (Scheme 24).[‌86‌] O/Se Acetal 30 reacts readily with a range of alcohols in the presence of copper(II) chloride, generating the corresponding acetals 31 in high yields. This procedure can also be used for the selective protection of diols.

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