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Synfacts 2011(12): 1313-1313
DOI: 10.1055/s-0031-1289360
DOI: 10.1055/s-0031-1289360
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Asymmetric α-Allylation of Aldehydes with Simple Allylic Alcohols
Contributor(s):Mark Lautens, Patrick T. FrankeG. Jiang, B. List*
Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
Direct Asymmetric α-Allylation of Aldehydes with Simple Allylic Alcohols Enabled by the Concerted Action of Three Different Catalysts
Angew. Chem. Int. Ed. 2011, 50: 9471-9474
Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
Direct Asymmetric α-Allylation of Aldehydes with Simple Allylic Alcohols Enabled by the Concerted Action of Three Different Catalysts
Angew. Chem. Int. Ed. 2011, 50: 9471-9474
Further Information
Publication History
Publication Date:
18 November 2011 (online)
Key words
allylation - chiral counteranions - palladium
Significance
List and co-workers developed an enantioselective direct α-allylation of α-branched aldehydes with allylic alcohols generating products with all-carbon quaternary stereogenic centers in high yields and excellent enantioselectivities. The general reaction scale for this transformation is 0.2 mmol.
Comment
It is suggested that the high enantioselectivity for the described transformation arises from an asymmetric counteranion-directed catalysis (ACDC) complex - three different catalytic species are involved: [Pd(PPh3)4], the chiral Brønsted acid TRIP, and benzhydryl amine.