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Molecules 2001, 6(1), 1-12; doi:10.3390/60100001
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Synthesis of Polycyclic Ring Systems Using Transition Metal Catalyzed Cyclizations of Diazo Alkynyl Ketones

Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA
Received: 3 November 2000 / Accepted: 6 November 2000 / Published: 22 December 2000
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Abstract

The rhodium(II)-catalyzed reaction of α-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 π-bond to give a vinyl carbenoid intermediate. The resulting rhodium complex undergoes a wide assortment of reactions including cyclopropanation, 1,2-hydrogen migration, CH-insertion, 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: rhodium; catalyst; diazo; ketone; alkyne; cyclization; CH-insertion; ylide; furo[3; 4-c]furans rhodium; catalyst; diazo; ketone; alkyne; cyclization; CH-insertion; ylide; furo[3; 4-c]furans
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Padwa, A. Synthesis of Polycyclic Ring Systems Using Transition Metal Catalyzed Cyclizations of Diazo Alkynyl Ketones. Molecules 2001, 6, 1-12.

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