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Organocatalytic Asymmetric α-Allylation and Propargylation of α-Branched Aldehydes with Alkyl Halides

Masanori Yoshida*

*Liberal Arts and Sciences, National Institute of Technology (KOSEN), Asahikawa College Shunkodai 2 jo 2-1-6, Asahikawa, Hokkaido 071-8142, Japan, Email: yoshidaedu.asahikawa-nct.ac.jp

M. Yoshida, J. Org. Chem., 2021, 86, 10921-10927.

DOI: 10.1021/acs.joc.1c01394 (free Supporting Information)


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Abstract

A chiral primary amino acid organocatalyst mediates an enantioselective α-allylation and -propargylation of α-branched aldehydes with alkyl halides in a good yield and high enantioselectivity to furnish α-allylated or -propargylated aldehydes with chiral quaternary carbon stereocenters. The reaction proceeded smoothly in a mildly basic aqueous solution of potassium hydrogen carbonate.

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proposed mechanism



Key Words

allylation of carbonyl compounds, organocatalysis


ID: J42-Y2021