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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

Contributor(s):
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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Further Information

Publication History

Publication Date:
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.


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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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