Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 13, Pages 8764-8772Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00581
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Funding
- National Natural Science Foundation of China [21762021, 21778025, 21762025, 21562026]
- Key Projects of Natural Science Foundation of Jiangxi Province [20192ACBL20026]
- Jiangxi Provincial Natural Science Foundation [20202BABL203007]
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An efficient and general base-promoted reaction for the synthesis of (Z)-beta-chloro-enamides using 1,1-dichloroalkenes and secondary sulfonamides or amides has been described. This reaction exhibits excellent functional group tolerance under simple and mild conditions. Mechanistic study suggests that the stereoselective trans-hydroamidation of alkynyl chlorides generated in situ from 1,1-dichloroalkenes is the key step.
An efficient and general base-promoted reaction of 1,1-dichloroalkenes with secondary sulfonamides and amides for the synthesis of (Z)-beta-chloro-enamides has been described. This reaction exhibits functional group tolerance under simple and mild conditions. Mechanistic study indicated that a stereoselective trans-hydroamidation of alkynyl chlorides generated in situ from 1,1-dichloroalkenes was the key step.
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