Synfacts 2020; 16(12): 1425
DOI: 10.1055/s-0040-1719546
Metals in Synthesis

Asymmetric Synthesis of Amino Alcohols Using a Catalytically Formed Chiral Auxiliary

Contributor(s):
Mark Lautens
,
Joachim Loup
Buzzetti L, Puriņš M, Greenwood PD. G, Waser J. * École Polytechnique Fédérale de Lausanne, Switzerland
Enantioselective Carboetherification/Hydrogenation for the Synthesis of Amino Alcohols via a Catalytically Formed Chiral Auxiliary.

J. Am. Chem. Soc. 2020;
142: 17334-17339
DOI: 10.1021/jacs.0c09177.
 

Significance

Waser and co-workers report the use of a catalytically formed chiral auxiliary for the asymmetric synthesis of amino alcohols. A palladium-catalyzed enantioselective carboetherification of propargylic amines using a trifluoroacetaldehyde-derived tether provided chiral oxazolidines. A diastereoselective hydrogenation of the tetrasubstituted olefin, followed by removal of the tether molecule, delivered valuable enantioenriched amino alcohols.


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Comment

Key to success was the use of a truncated monophosphine Trost-type ligand. Interestingly, all four stereoisomers of the product could be obtained by the choice of the chiral ligand and the substituents on the readily available propargylic amines. It is noteworthy that the resulting diaryl-substituted amino alcohols are found in many bioactive molecules.


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Publication History

Publication Date:
17 November 2020 (online)

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