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

Albert Padwaemail
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA
Received: 3 November 2000 / Accepted: 6 November 2000 / Published: 22 December 2000
PDF Full-text Download PDF Full-Text [105 KB, uploaded 3 October 2008 13:54 CEST]
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

Article Statistics

Click here to load and display the download statistics.

Cite This Article

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.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert