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: petasis
usc.edu
F. Liepouri, G. Bernasconi, N. A. Petasis, Org. Lett., 2015, 17, 1628-1631.
DOI: 10.1021/acs.orglett.5b00024
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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
