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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Melnikov, Mikhail Ya Trushkov, Igor V. Villemson, Elena V. Ivanova, Olga A. Budynina, Ekaterina M. Ivanov, Konstantin L. |
| Description | Author Affiliation: Ivanov KL ( Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow, 119991 (Russia), Fax: (+7) 4959391814.) |
| Abstract | A general method for ring opening of various donor–acceptor cyclopropanes with the azide ion through an $S_{N}2-like$ reaction has been developed. This highly regioselective and stereospecific process proceeds through nucleophilic attack on the more-substituted C2 atom of a cyclopropane with complete inversion of configuration at this center. Results of DFT calculations support the $S_{N}2$ mechanism and demonstrate good qualitative correlation between the relative experimental reactivity of cyclopropanes and the calculated energy barriers. The reaction provides a straightforward approach to a variety of polyfunctional azides in up to 91 % yield. The high synthetic utility of these azides and the possibilities of their involvement in diversity-oriented synthesis were demonstrated by the developed multipath strategy of their transformations into five-, six-, and seven-membered N-heterocycles, as well as complex annulated compounds, including natural products and medicines such as (−)-nicotine and atorvastatin. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 13 |
| Volume Number | 21 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2015-03-23 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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