EventsThe 4th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-4-01782
This submission belongs to the session a. General Organic Synthesis of the event The 4th International Electronic Conference on Synthetic Organic Chemistry
Published date
11 Sep, 2000
Citation
Albert Padwa, Synthesis of Polycyclic Ring Systems Using Transition Metal Catalyzed Cyclizations of Diazo Alkynyl Ketones, in Proceedings of The 4th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2000, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-4-01782
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Synthesis of Polycyclic Ring Systems Using Transition Metal Catalyzed Cyclizations of Diazo Alkynyl Ketones

Albert Padwa 1
1. Department of Chemistry, Emory University, Atlanta, GA 30322 USA
Abstract
The rhodium(II)-catalyzed reaction of a-diazo ketones bearing tethered alkyne units represents a new and useful method for the construction of a variety of substituted cyclopentenones. The process proceeds by addition of the rhodium-stabilized carbenoid onto the acetylenic pi-bond to give a vinyl carbenoid intermediate. The resulting rhodium complex undergoes a wide assortment of reactions including cyclopropanation, 1,2-hydrogen migration, CHinsertion, addition to tethered alkynes and ylide formation. When 2-alkynyl-2-diazo-3-oxobutanoates were treated with a Rh(II)-catalyst, furo[3,4-c]furans were formed in excellent yield.
Keywords
n/a
New heterocyclic materials
3-Dimethylaminopropenoates and Related Compounds in the Synthesis of Heterocyclic Systems and Heterocyclic Amino Acids