Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 44, Pages 10319-10322Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201902767
Keywords
asymmetric synthesis; atropisomers; axial chirality; organocatalyst; pot-economy
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Funding
- JSPS KAKENHI [JP18H04641]
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A three-pot synthetic method that features the use of an organocatalyst as the key step was developed for the preparation of biaryl atropisomers. The first reaction is an asymmetric domino Michael-Henry reaction catalyzed by diphenylprolinol silyl ether to afford the substituted nitrocyclohexanecarbaldehyde with four stereogenic centers and one defined configuration of a stereogenic axis with excellent enantioselectivity. Removal of the central chirality from the domino products afforded biaryl atropisomers having axial chirality with excellent enantioselectivity.
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