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One-Pot, Tandem Wittig Hydrogenation: Formal C(sp3)-C(sp3) Bond Formation with Extensive Scope

Rory Devlin, David J. Jones and Gerard P. McGlacken*

*School of Chemistry and Analytical and Biological Chemistry Research Facility (ABCRF), University College Cork, Cork T12 YN60, Ireland, Email: g.mcglackenucc.ie

R. Devlin, D. J. Jones, G. P. McGlacken, Org. Lett., 2020, 22, 5223-5228.

DOI: 10.1021/acs.orglett.0c01874 (free Supporting Information)


Abstract

A one-pot, tandem Wittig hydrogenation of aldehydes with stabilized ylides enables a formal C(sp3)-C(sp3) under mild conditions. The reaction is high yielding and broad in scope. Early insights suggest that the chemoselectivity observed in the reduction step is due to partial poisoning of the catalyst.


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Key Words

Wittig reaction, esters, hydrogen


ID: J54-Y2020