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Transition Metal-Catalyzed Reactions of 3-Aza-2-oxabicyclo[2.2.1]hept-5-enes

[ Vol. 15 , Issue. 6 ]

Author(s):

Katrina Tait and William Tam*   Pages 762 - 780 ( 19 )

Abstract:


Background: Transition metal catalysts are becoming increasingly more important in organic synthesis and are being used to catalyze novel reactions that allow for more efficient synthesis of many pharmaceuticals. Transition metal-catalyzed reactions of 3-aza-2-oxabicyco[2.2.1]hept-5-enes provide efficient synthetic pathways to generate a diverse range of biologically and synthetically useful products. 3-Aza-2- oxabicyclic alkenes undergo three main types of reactions: reductive N-O bond cleavage, C-O bond cleavage, and modification of the alkene component.

Objective: The purpose of this review is to summarize and discuss the transition metal-mediated reactions of 3- aza-2-oxabicyclo[2.2.1]hept-5-enes, including the mechanisms of reactions based on the transition metal used, the different stereo- and regiochemical outcomes of reactions with this asymmetrical substrate, and the biological importance of exploring these reactions.

Conclusion: It is clear from the review of the topic that a vast amount of work has been done in this area, and transition metals have been used to control the regio- and stereoselective reactions of 3-aza-2-oxabicyclic alkenes to create biologically active and synthetically useful products. The transition metal-catalyzed reactions of 3-aza-2-oxabicyclic alkenes proceed through three general reactions: through cleavage of the N-O bond, cleavage of the C-O bond, and modification of the alkene component. Without the use of transition metals, the substrate would not be activated and these reactions would not be possible. The use of transition metals opens up an array of new reactions that have the ability to create different functional groups with different regio- and stereoselectivities based on the metal and conditions used. The products made through these transition metalcatalyzed reactions can be useful as antibiotics, siderophores, and carbocyclic nucleosides such as noraristeromycin and carbocyclic polyoxin C.

Keywords:

Transition metal, bicyclic alkene, ring-opening, stereoselective, metal catalysis, regioselective.

Affiliation:

Guelph-Waterloo Center for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Guelph-Waterloo Center for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1

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