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Please login or sign up for a free trial to access the full content. Method 2: Synthesis from Glycols

DOI: 10.1055/sos-SD-025-00101

Kalesse, M.Science of Synthesis, (200725139.

Carbon-skeleton rearrangement reactions are very powerful synthetic tools for the construction of new carbon frameworks and many reactions have been developed so far. Among them, is the pinacol rearrangement, which is one of the oldest-known transformations of the carbon skeleton. When vicinal diols (glycols), e.g. 16 or 18, are treated with either Brønsted or Lewis acids, rearranged aldehydes, e.g. 17 or 19, or ketones can be obtained, although elimination without rearrangement can be a side reaction.[‌5‌,‌6‌] Generally, aldehyde formation is favored by the use of mild conditions (lower temperatures, weaker acids) (Scheme 5).

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