Templated assembly of chiral medium-sized cyclic ethers via 8-endo-trig nucleophilic cyclization of cyclopropenes
An efficient approach toward enantioenriched eight-membered heterocycles via the intramolecular formal substitution of bromocyclopropanes with oxygen-based nucleophiles has been developed. The reaction proceeds via a reactive cyclopropene intermediate, which undergoes a rapid 8-endo-trig cyclization...
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American Chemical Society
2018
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ir-20.500.12258-31642020-07-30T13:37:56Z Templated assembly of chiral medium-sized cyclic ethers via 8-endo-trig nucleophilic cyclization of cyclopropenes Rubin, M. A. Рубин, М. А. Cyclopropane derivative Cyclopropenes Ether derivative Chemical structure Cyclization Molecular structure Particle size An efficient approach toward enantioenriched eight-membered heterocycles via the intramolecular formal substitution of bromocyclopropanes with oxygen-based nucleophiles has been developed. The reaction proceeds via a reactive cyclopropene intermediate, which undergoes a rapid 8-endo-trig cyclization affording cis-fused [6.1.0] bicyclic products exclusively. The quaternary chiral center in the cyclopropene governs the configuration of the other two stereocenters in the final product 2018-10-09T09:33:03Z 2018-10-09T09:33:03Z 2016 Статья Ryabchuk, P., Matheny, J.P., Rubina, M., Rubin, M. Templated Assembly of Chiral Medium-Sized Cyclic Ethers via 8-endo-trig Nucleophilic Cyclization of Cyclopropenes // Organic Letters. - 2016. - Volume 18. - Issue 24. -Pages 6272-6275 https://www.scopus.com/record/display.uri?eid=2-s2.0-85006341889&origin=resultslist&sort=plf-f&src=s&nlo=&nlr=&nls=&sid=2d4e826478140d99650a215e37019390&sot=aff&sdt=cl&cluster=scopubyr%2c%222016%22%2ct&sl=174&s=AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29+OR+AF-ID%28%22Stavropol+State+University%22+60070961%29+OR+AF-ID%28%22stavropolskij+Gosudarstvennyj+Tehniceskij+Universitet%22+60026323%29&relpos=2&citeCnt=3&searchTerm= http://hdl.handle.net/20.500.12258/3164 en Organic Letters application/pdf application/pdf American Chemical Society |
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| language |
English |
| topic |
Cyclopropane derivative Cyclopropenes Ether derivative Chemical structure Cyclization Molecular structure Particle size |
| spellingShingle |
Cyclopropane derivative Cyclopropenes Ether derivative Chemical structure Cyclization Molecular structure Particle size Rubin, M. A. Рубин, М. А. Templated assembly of chiral medium-sized cyclic ethers via 8-endo-trig nucleophilic cyclization of cyclopropenes |
| description |
An efficient approach toward enantioenriched eight-membered heterocycles via the intramolecular formal substitution of bromocyclopropanes with oxygen-based nucleophiles has been developed. The reaction proceeds via a reactive cyclopropene intermediate, which undergoes a rapid 8-endo-trig cyclization affording cis-fused [6.1.0] bicyclic products exclusively. The quaternary chiral center in the cyclopropene governs the configuration of the other two stereocenters in the final product |
| format |
Статья |
| author |
Rubin, M. A. Рубин, М. А. |
| author_facet |
Rubin, M. A. Рубин, М. А. |
| author_sort |
Rubin, M. A. |
| title |
Templated assembly of chiral medium-sized cyclic ethers via 8-endo-trig nucleophilic cyclization of cyclopropenes |
| title_short |
Templated assembly of chiral medium-sized cyclic ethers via 8-endo-trig nucleophilic cyclization of cyclopropenes |
| title_full |
Templated assembly of chiral medium-sized cyclic ethers via 8-endo-trig nucleophilic cyclization of cyclopropenes |
| title_fullStr |
Templated assembly of chiral medium-sized cyclic ethers via 8-endo-trig nucleophilic cyclization of cyclopropenes |
| title_full_unstemmed |
Templated assembly of chiral medium-sized cyclic ethers via 8-endo-trig nucleophilic cyclization of cyclopropenes |
| title_sort |
templated assembly of chiral medium-sized cyclic ethers via 8-endo-trig nucleophilic cyclization of cyclopropenes |
| publisher |
American Chemical Society |
| publishDate |
2018 |
| url |
https://www.scopus.com/record/display.uri?eid=2-s2.0-85006341889&origin=resultslist&sort=plf-f&src=s&nlo=&nlr=&nls=&sid=2d4e826478140d99650a215e37019390&sot=aff&sdt=cl&cluster=scopubyr%2c%222016%22%2ct&sl=174&s=AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29+OR+AF-ID%28%22Stavropol+State+University%22+60070961%29+OR+AF-ID%28%22stavropolskij+Gosudarstvennyj+Tehniceskij+Universitet%22+60026323%29&relpos=2&citeCnt=3&searchTerm= https://dspace.ncfu.ru/handle/20.500.12258/3164 |
| work_keys_str_mv |
AT rubinma templatedassemblyofchiralmediumsizedcyclicethersvia8endotrignucleophiliccyclizationofcyclopropenes AT rubinma templatedassemblyofchiralmediumsizedcyclicethersvia8endotrignucleophiliccyclizationofcyclopropenes |
| _version_ |
1760601782021521408 |