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Synfacts 2019; 15(09): 1023
DOI: 10.1055/s-0039-1690549
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

HCN-Free Hydrocyanation of Alkenes

Rezensent(en):
Paul Knochel
,
Ferdinand H. Lutter
Li X, You C, Yang J, Li S, Zhang D, Lv H. * Zhang X. * Wuhan University and Southern University of Science and Technology, Shenzhen, P. R. of China
Asymmetric Hydrocyanation of Alkenes without HCN.

Angew. Chem. Int. Ed. 2019;
58: 10928-10931
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Publikationsverlauf

Publikationsdatum:
20. August 2019 (online)

 
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Key words

asymmetric synthesis - hydrocyanation - rhodium catalysis

Significance

The authors developed an asymmetric rhodium-catalyzed HCN-free formal hydrocyanation of various functionalized 1,2- and 1,1-disubstituted alkenes. Depended on the alkene, various chiral ligands are necessary to afford the corresponding chiral products in high enantioselectivities.


 

Comment

The formal asymmetric hydrocyanation proceeds via an asymmetric hydroformylation and subsequent acid-catalyzed imine formation with 1-aminopiperidine. An aza-Cope elimination induced by addition of MMPP affords the corresponding chiral nitrile.


 

 


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