Molecules 2001, 6(1), 1-12; doi:10.3390/60100001
Review

Synthesis of Polycyclic Ring Systems Using Transition Metal Catalyzed Cyclizations of Diazo Alkynyl Ketones

Received: 3 November 2000; Accepted: 6 November 2000 / Published: 22 December 2000
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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
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MDPI and ACS Style

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

AMA Style

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

Chicago/Turabian Style

Padwa, Albert. 2001. "Synthesis of Polycyclic Ring Systems Using Transition Metal Catalyzed Cyclizations of Diazo Alkynyl Ketones." Molecules 6, no. 1: 1-12.

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