C-C Coupling of Acyclic Nitronates with Silyl Ketene Acetals under Silyl Triflate Catalysis: Reactivity Umpolung of Aliphatic Nitro Compounds (Eur. J. Org. Chem. 18/2012)

• Published in: European journal of organic chemistry 2012-06, Vol.2012 (18), p.n/a
• Main Authors: Smirnov, Vladimir O., Khomutova, Yulia A., Tartakovsky, Vladimir A., Ioffe, Sema L.
• Format: Article
• Language: English
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201290045

The cover picture shows the jet engine of a Fokker 100 in its ordinary and reverse thrust modes. These thrust modes closely resemble the chemistry of nitroalkenes when a new approach for the umpolung of their conventional reactivity is taken into account. Just like the deployment of the two buckets from the jet engine nozzle induces a reverse thrust, quenching of the negative charges on the two oxygen atoms of the nitronate anion with alkyl or silyl groups generates an electrophilic center on the former nucleophilic α‐carbon atom of the nitroalkane, which induces reversed reactivity. Details of this new approach are described in the article by V. O. Smirnov, S. L. Ioffe et al. on p. 3377 ff. magnified image