Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 14, Pages 9270-9281Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01416
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Funding
- National Natural Science Foundation of China [21672176, 21332007]
- National Key RAMP
- D Program of China [2017YFA0207302]
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An efficient and mild protocol for the direct and flexible synthesis of 3-amino-1,4-diynes bearing an aza-quaternary carbon from tertiary amides and lactams has been established. The one-pot method consists of in situ activation of amides with trifluoromethanesulfonic anhydride, followed by double addition of alkynyllithium reagents at a concentration of 0.5 mol.L-1 in dichloromethane. This constitutes an extension of the method of direct reductive bisalkylation of amides that allows both employing alkynyllithium reagents as the first-addition nucleophiles and incorporating an alkynyl group as the first- introduced group.
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