Asymmetric α-Allylation of Aldehydes with Simple
Allylic Alcohols

G. Jiang; B. List

doi:10.1055/s-0031-1289360

Synfacts, Table of Contents

Synfacts 2011(12): 1313-1313
DOI: 10.1055/s-0031-1289360

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Asymmetric α-Allylation of Aldehydes with Simple Allylic Alcohols

Contributor(s):Mark Lautens, Patrick T. Franke

G. 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

Abstract

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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.

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