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Diastereoselective Aza-Mislow-Evans Rearrangement of N-Acyl-tert-Butanesulfinamides into α-Sulfenyloxy Carboxamides.

A new interesting article has been published in Angew Chem Int Ed Engl. 2018 Sep 26. doi: 10.1002/anie.201809551. and titled:

Diastereoselective Aza-Mislow-Evans Rearrangement of N-Acyl-tert-Butanesulfinamides into α-Sulfenyloxy Carboxamides.

Authors of this article are:
Tang F Yao Y Xu YJ Lu CD.

A summary of the article is shown below:
A diastereoselective [2,3]-rearrangement of O-silyl N-sulfinyl N,O-ketene acetals derived from chiral N-acyl-tert-butanesulfinamides was developed, giving α-sulfenyloxyl carboxamides with excellent enantioselectivities. Enolization and subsequent silylation of N-acyl-tert-butanesulfinamides initiate the aza-variant of Mislow-Evans rearrangement, in which the chirality of the sulfur in the rearrangement precursors is faithfully transferred to the α-carbon stereocenter of the products. Ellman’s sulfinamide, often used as a chiral ammonia equivalent, can serve in this rearrangement as a chiral precursor for the asymmetric synthesis of α-oxygen-functionalized carboxamides.

Check out the article’s website on Pubmed for more information:



This article is a good source of information and a good way to become familiar with topics such as: diastereoselective, rearrangement, asymmetric, N-acyl-tert-butanesulfinamides, α-sulfenyloxylated amides.

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