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Component-Selective and Stereocontrolled One-Step Three-Component Reaction among Aldehydes, Amines, and Allenyl Boronic Acids or Allenyl Pinacolboronates

Fotini Liepouri, Giovanni Bernasconi and Nicos A. Petasis*

*Department of Chemistry and Loker Hydrocarbon Research Institute, University of Southern California, Los Angeles, California 90089, United States, Email: petasisusc.edu

F. Liepouri, G. Bernasconi, N. A. Petasis, Org. Lett., 2015, 17, 1628-1631.

DOI: 10.1021/acs.orglett.5b00024 (free Supporting Information)


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Abstract

A one-step, three-component condensation of allenyl boronic acids or allenyl pinacolboronates with amines and aldehydes affords α-allenyl or α-propargyl α-amino acids and anti-β-amino alcohols. Secondary amines generate exclusively α-allenyl α-amino acids, while primary aliphatic amines lead to α-propargyl α-amino acids.

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Key Words

Petasis reaction, Multicomponent Reactions, Allenes, Propargylation


ID: J54-Y2015