Cyclopropanes and hypervalent iodine reagents: high energy compounds for applications in synthesis and catalysis.
One of the major challenges faced by organic chemistry is the efficient synthesis of increasingly complex molecules. Since October 2007, the Laboratory of Catalysis and Organic Synthesis (LCSO) at EPFL has been working on the development of catalytic reactions based on the Umpolung of the innate reactivity of functional groups. Electrophilic acetylene synthons have been developed using the exceptional properties of ethynyl benziodoxolone (EBX) hypervalent iodine reagents for the alkynylation of heterocycles and olefins. The obtained acetylenes are important building blocks for organic chemistry, material sciences and chemical biology. The ring-strain energy of donor-acceptor cyclopropanes was then used in the first catalytic formal homo-Nazarov cyclization. In the case of aminocyclopropanes, the method could be applied in the synthesis of the alkaloids aspidospermidine and goniomitine. The developed methods are expected to have a broad potential for the synthesis and functionalization of complex organic molecules, including carbocycles and heterocycles.
Ecole Polytechnique Fédérale de Lausanne, Laboratory of Catalysis and Organic Synthesis, EPFL SB ISIC LCSO, BCH 4306, CH-1015 Lausanne.
Davinia
D
Fernández González
Filippo
F
De Simone
Jonathan P
JP
Brand
Stefano
S
Nicolai
Jérôme
J
Waser
D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D015394:Molecular Structure; D013816:Thermodynamics
D000480:Alkynes; D003521:Cyclopropanes; D006847:Hydrocarbons, Iodinated