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Gold-catalyzed 1,3-transposition of ynones.

Kazem Shiroodi R, Soltani M, Gevorgyan V - J. Am. Chem. Soc. (2014)

Bottom Line: An efficient, regioselective gold-catalyzed 1,3-transposition reaction of ynones and diynones has been developed.It was found that stereoelectronic (interrupted conjugation) and electronic (extended conjugation) factors could efficiently govern the regioselectivity of this thermodynamically controlled transformation.The produced conjugated diynones were efficiently transformed into diverse alkyne-substituted five- and six-membered heterocycles.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60608-7061, United States.

ABSTRACT
An efficient, regioselective gold-catalyzed 1,3-transposition reaction of ynones and diynones has been developed. It was found that stereoelectronic (interrupted conjugation) and electronic (extended conjugation) factors could efficiently govern the regioselectivity of this thermodynamically controlled transformation. The produced conjugated diynones were efficiently transformed into diverse alkyne-substituted five- and six-membered heterocycles.

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Metal-Catalyzed 1,3-Transposition of Functional Groups
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Gold-catalyzed 1,3-transposition of ynones.

Kazem Shiroodi R, Soltani M, Gevorgyan V - J. Am. Chem. Soc. (2014)

Metal-Catalyzed 1,3-Transposition of Functional Groups
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4206192&req=5

sch1: Metal-Catalyzed 1,3-Transposition of Functional Groups
Bottom Line: An efficient, regioselective gold-catalyzed 1,3-transposition reaction of ynones and diynones has been developed.It was found that stereoelectronic (interrupted conjugation) and electronic (extended conjugation) factors could efficiently govern the regioselectivity of this thermodynamically controlled transformation.The produced conjugated diynones were efficiently transformed into diverse alkyne-substituted five- and six-membered heterocycles.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60608-7061, United States.

ABSTRACT
An efficient, regioselective gold-catalyzed 1,3-transposition reaction of ynones and diynones has been developed. It was found that stereoelectronic (interrupted conjugation) and electronic (extended conjugation) factors could efficiently govern the regioselectivity of this thermodynamically controlled transformation. The produced conjugated diynones were efficiently transformed into diverse alkyne-substituted five- and six-membered heterocycles.

Show MeSH
Related in: MedlinePlus