A set of (3-chloroprop-1-en-1-yl)boronates 10 were synthesised, starting from (3-chloroprop-1-en-1-yl)bis(isopinocampheyl)borane. Quaternisation of 10 by Grignard methodology afforded “ate” species 14, which underwent spontaneous anionotropic rearrangement to give the substituted allylboronates 15. By a suitable choice of the diol component in 10 and of the reaction temperature, α- or γ-substituted allylboronates 15 or 16 could be selectively produced, offering routes to homoallylic alcohols 9 or anti-8, respectively, after treatment with an aldehyde. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
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Lombardo et al. (2002) studied this question.