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Gold(I)-catalyzed, stereocontrolled enamide synthesis from primary amides and propargyl aldehydes using a tandem strategy

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Title
Gold(I)-catalyzed, stereocontrolled enamide synthesis from primary amides and propargyl aldehydes using a tandem strategy
Author(s)
Sang Min Kim; Dabon Lee; Soon Hyeok Hong
Publication Date
2014-12
Journal
ORGANIC LETTERS, v.16, no.23, pp.6168 - 6171
Publisher
AMER CHEMICAL SOC
Abstract
A novel strategy for enamide synthesis from primary amides and propargyl aldehydes via Au(I)-catalyzed tandem amide addition and Meyer−Schuster rearrangement is described. In situ generated hemiaminals were successfully converted to the desired products under the optimized conditions. Enamide stereochemistry was controlled simply by changing solvents and adding a catalytic amount of acid. The developed synthetic strategy provides a new method to synthesize various β-substituted α,β-unsaturated carbonyl compounds.
URI
https://pr.ibs.re.kr/handle/8788114/854
DOI
10.1021/ol503055x
ISSN
1523-7060
Appears in Collections:
Center for Nanoparticle Research(나노입자 연구단) > 1. Journal Papers (저널논문)
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