Journal
ACS CATALYSIS
Volume 10, Issue 23, Pages 13820-13824Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c04223
Keywords
enantioselective catalysis; copper catalysis; alkynylation; nitrogen heterocycles; Hammett correlation
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Funding
- NIH funding (NSF) [CHE0421224, CHE1229234, CHE0840401, CHE1048367]
- NIH [P20 GM104316, P20 GM103541, S10 OD016267]
- NSF [CHE1664981]
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An enantioselective copper-catalyzed alkynylation of unstabilized cyclic iminium ions has been developed. Whereas such alkynylations typically utilize pyridinium, quinolinium, and isoquinolinium intermediates, this method enables use of cyclic iminium ions unstabilized by resonance. With the use of a Lewis acid and copper catalyst, these iminium ions are generated in situ from readily available hemiaminal methyl ethers and transformed into highly enantioenriched alpha-alkynylated cyclic amines. A variety of terminal al es can be incorporated in high yields and enantiomeric excesses.
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