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Synfacts 2014; 10(5): 0488
DOI: 10.1055/s-0033-1341173
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Stereodivergent Synthesis of Labile Aldehydes via a Dual Catalysis Approach

Contributor(s):
Mark Lautens
,
David A. Petrone
Krautwald S, Schafroth MA, Sarlah D, Carreira EM * ETH Zürich, Switzerland
Stereodivergent α‑Allylation of Linear Aldehydes with Dual Iridium and Amine Catalysis.

J. Am. Chem. Soc. 2014;
136: 3020-3023
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Publication History

Publication Date:
17 April 2014 (online)

 
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Key words

iridium - amine catalysis - aldehydes

Significance

The enantioselective allylic alkylation has found widespread application in the syntheses of many complex targets. However, the introduction of more difficult classes of nucleophiles is important to continue to push this field forward. This approach uses iridium/amine dual catalysis to introduce aldehyde nucleophiles, to selectively and mildly form products which are stereochemically labile.


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Comment

The authors present a stereodivergent Ir(P,olefin)/chiral amine catalyzed α-allylation of linear aldehydes. Through a combinatorial catalyst–ligand strategy, all four stereoisomers of these stereochemically labile α,β-chiral γ,δ-unsaturated aldehydes can be accessed. The authors applied this methodology to the synthesis of (–)-paroxetine.


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