Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 38, Pages 12347-12351Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201807735
Keywords
chemoselectivity; cyanation; hydrosilylation; molybdenum; reductive functionalization
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Funding
- Umea University
- K&A Wallenberg Foundations
- Swedish Research Council
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The selective reduction of amides into an intermediate hemiaminal catalyzed by Mo(CO)(6) together with the inexpensive and easy to handle TMDS (1,1,3,3-tetramethyldisiloxane) as reducing agent, followed by subsequent trapping of the hemiaminal with a cyanide source, allows for the straightforward synthesis of alpha-amino nitriles. The methodology presented here, displays high levels of chemoselectivity allowing for the reduction of amides in the presence of functional groups such as ketones, imines, aldehydes, and acids, which affords a simple route for the synthesis of alpha-amino nitriles with a broad scope of functionalities in high yields. Furthermore, the applicability of this methodology is demonstrated by scale up experiments and by derivatization of the target compounds into synthetically interesting products. The selective cyanation is successfully applied in late stage functionalizations of amide containing drugs and prolinol derivatives.
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