Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 20, Pages 9407-9412Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo301772f
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Funding
- DST, New Delhi [SR-S1/OC-60/2011]
- BRNS, DAE, Government of India [2012/37C/3/BRNS]
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Hydroamidation of electron-deficient terminal alkynes by amides in presence of Pd catalyst has been exploited for the stereoselective synthesis of Z-enamides. The possible intramolecular hydrogen bonding between the amido proton and carbonyl oxygen of ester group provides the extra stability to the Z-isomer of vinyl palladium complex, which subsequently undergoes protodepalladation and leads to the Z-enamide selectively. This process is found to be mild and operationally simple with broad substrate scope.
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