Asymmetric Synthesis of β,β-Disubstituted Alanines via a Sequential C(sp2)–C(sp3) Cross-Coupling–Hydrogenation Strategy

We report the development of a sequential C­(sp2)–C­(sp3) Suzuki cross-coupling–asymmetric hydrogenation strategy which allows access to a diverse array of valuable β,β-disubstituted alanine derivatives. This synthesis exhibits broad functional group tolerance, and permits efficient access to β-aryl...

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Bibliographic Details
Published in:Organic letters 2024-07, Vol.26 (29), p.6284-6289
Main Authors: Petrone, David A., Maturano, Jonathan, Herbort, James, Plasek, Erin E., Vivaldo-Nikitovic, J. Mayeli, Sarlah, David
Format: Article
Language:English
Subjects:
alanine
enantioselectivity
hydrogenation
stereoselective synthesis
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Summary:We report the development of a sequential C­(sp2)–C­(sp3) Suzuki cross-coupling–asymmetric hydrogenation strategy which allows access to a diverse array of valuable β,β-disubstituted alanine derivatives. This synthesis exhibits broad functional group tolerance, and permits efficient access to β-aryl-β-alkyl, and the more rarely reported β,β-dialkyl Ala derivatives with high yield and excellent enantioselectivity. This transformation has been exhibited on decagram quantity, and can be used to generate Fmoc amino acid derivatives which are useful for SPPS.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c02376