N-Sulfonyltriazoles as Carbene Precursors

Emory University, Atlanta GA

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Abstract

? DESCRIPTION (provided by applicant): The central goal of this research program is to develop new strategic reactions that will have broad impact in organic synthesis and on the methods used for the synthesis of new pharmaceutical agents. The particular area of emphasis will be on rhodium- stabilized carbenoids containing both donor and acceptor groups, which are capable of a range of synthetically useful transformations. The chemistry of these carbenoids is unusually rich and has resulted in several new strategic reactions for synthesis. In order to develop this chemistry fully it will be necessary to expand the range of donor groups that can be used. The traditional approach to the donor/acceptor carbenes is from diazo compounds, and this limits the type of donor groups to aryl, heteroaryl, and some alkenyl derivatives. In this proposal focuses on the use of N-sulfonyltriazoles to broaden the scope of donor/acceptor carbenes with a particular emphasis on the development of amino- and alkoxy substituted carbene derivatives. It is projected that these studies will result in the development of new synthetic methods that are distinct from those possible with the established rhodium carbenes derived from diazoacetates. These methods will be showcased by their use in the synthesis of biologically relevant natural products and important pharmaceutical drug scaffolds.