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Synfacts 2017; 13(07): 0753
DOI: 10.1055/s-0036-1590529
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Acyloin Rearrangement of α-Hydroxy Acetals to α-Alkoxy Ketones

Contributor(s):
Benjamin List
,
Denis Höfler
Wu H. Wang Q. Zhu J. * École Polytechnique Fédérale de Lausanne, Switzerland
Organocatalytic Enantioselective Acyloin Rearrangement of α-Hydroxy Acetals to α-Alkoxy Ketones.

Angew. Chem. Int. Ed. 2017;
56: 5858-5861
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Further Information

Publication History

Publication Date:
19 June 2017 (online)

 
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Key words

acyloin rearrangement - hydroxy acetals - chiral phosphoramides

Significance

The group of Zhu reports an ­organocatalytic asymmetric acyloin rearrangement of disubstituted α-hydroxy acetals. This rearrangement is carried out in the presence of a chiral N-triflyl phosphoramide catalyst to give the desired α-alkoxy ketones in good to high yields and high to excellent enantioselectivities.


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Comment

The acyloin (α-ketol) rearrangement is employed in the biosynthesis of many different natural products. The generation of an ion pair between the oxocarbenium ion and the chiral phosphoramide catalyst is presumably responsible for the asymmetric induction of this 1,2-carbon-shift reaction.


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