Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 3, Pages 1625-1628Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202011641
Keywords
alicyclic amines; annulation; C− H bond functionalization; C− C bond formation; Mannich reaction
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Funding
- NIH-NIGMS [R01GM101389]
- NIH [S10 OD021758-01A1]
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Despite efforts by practitioners, direct alpha-C-H bond functionalization of unprotected alicyclic amines is rare. A new method utilizing N-lithiated alicyclic amines has been developed, providing a convenient approach to achieve functionalization reactions under mild conditions. This method offers a new pathway for the synthesis of beta-amino ketones with regioselective alpha'-alkylation, and potential for one-pot synthesis of polycyclic dihydroquinolones.
Despite extensive efforts by many practitioners in the field, methods for the direct alpha-C-H bond functionalization of unprotected alicyclic amines remain rare. A new advance in this area utilizes N-lithiated alicyclic amines. These readily accessible intermediates are converted to transient imines through the action of a simple ketone oxidant, followed by alkylation with a beta-ketoacid under mild conditions to provide valuable beta-amino ketones with unprecedented ease. Regioselective alpha '-alkylation is achieved for substrates with existing alpha-substituents. The method is further applicable to the convenient one-pot synthesis of polycyclic dihydroquinolones through the incorporation of a SNAr step.
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