Diastereoselective synthesis of useful building blocks by crotylation of β-branched α-methylaldehydes with potassium crotyltrifluoroborates

Kyosuke Tanaka, Yukiko Fujimori, Yoko Saikawa, Masaya Nakata

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(Chemical Equation Presented) The diastereoselective construction of stereotriads having consecutive methyl, hydroxy, and methyl substituents was realized by the substrate-controlled crotylation of β-branched α-methylaldehydes with potassium crotyltrifluoroborates. Especially, crotylation of 2-(1,3-dithian-2-yl)propanal with potassium (E)- crotyltrifluoroborate afforded, in good yield and with excellent diastereoselectivity, a useful building block that has different and potential functional groups on both ends.

Original languageEnglish
Pages (from-to)6292-6298
Number of pages7
JournalJournal of Organic Chemistry
Issue number16
Publication statusPublished - 2008 Aug 15


ASJC Scopus subject areas

  • Organic Chemistry

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