Organic Letters
Organic Letters
5 years ago

Organocatalytic Synthesis of cis-2,3-Aziridine Aldehydes by a Postreaction Isomerization

Organocatalytic Synthesis of cis-2,3-Aziridine Aldehydes by a Postreaction Isomerization
Łukasz Albrecht, Maciej Saktura, Marta Romaniszyn, Piotr Drelich, Jan Bojanowski, Sebastian Frankowski
An unprecedented organocatalytic cis-selective aziridination of α,β-unsaturated aldehydes is described. The strategy utilizes postreaction isomerization as a key step. Our study demonstrates that by a proper choice of structural features of reagents and the catalyst the outcome of well-established reactions can be altered, leading to the formation of normally inaccessible diastereomers. The usefulness of the developed approach has been confirmed in the syn-selective formal aminohydroxylation of α,β-unsaturated aldehydes.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02634

DOI: 10.1021/acs.orglett.7b02634

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