Diastereoselectivity in the Carroll rearrangement of β-keto esters of tertiary allylic alcohols

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Abstract

Carroll rearrangement of β-keto esters derived from tertiary allylic alcohols, for example, 7, under basic conditions followed by decarboxylation of the resulting β-keto acids yielded the expected γ, δ-unsaturated methyl ketones 8 with a range of olefin geometries from 100:0 to 1:1.8 E/Z, depending on the relative steric requirements of the two groups at the allylic center. © 2003 Elsevier Ltd. All rights reserved.

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Jung, M. E., & Duclos, B. A. (2004). Diastereoselectivity in the Carroll rearrangement of β-keto esters of tertiary allylic alcohols. Tetrahedron Letters, 45(1), 107–109. https://doi.org/10.1016/j.tetlet.2003.10.102

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