Pregled bibliografske jedinice broj: 1003519
Regioselective 2-Imino-1, 3-thiazolidine vs. 2-Imino-1, 3-oxazolidine Formation from the Vicinalsec-Amino Alcohol of Desosamine
Regioselective 2-Imino-1, 3-thiazolidine vs. 2-Imino-1, 3-oxazolidine Formation from the Vicinalsec-Amino Alcohol of Desosamine // European journal of organic chemistry, 2013 (2013), 21; 4666-4673 doi:10.1002/ejoc.201300266 (međunarodna recenzija, članak, znanstveni)
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Naslov
Regioselective 2-Imino-1, 3-thiazolidine vs. 2-Imino-1, 3-oxazolidine Formation from the Vicinalsec-Amino Alcohol of Desosamine
Autori
Ištuk, Zorica Marušić ; Vujasinovi, Ines ; Čikoš, Ana ; Kragol, Goran
Izvornik
European journal of organic chemistry (1434-193X) 2013
(2013), 21;
4666-4673
Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni
Ključne riječi
Medicinal chemistry / Macrocycles / Heterocycles / Amino alcohols / Cyclization
Sažetak
In order to optimize Mukaiyama reagent-induced cyclization of vicinal sec-amino alcohols of desosamine origin towards exclusive formation of N′-substituted-2-imino-1, 3-thiazolidines via a thiocarbamoyl intermediate, the influence of reaction conditions was studied. A novel, mild, one-pot, two-step method was developed, and the formation of N′-substituted-2-imino-1, 3-oxazolidines as side products was minimized. The inversion of configuration at C-2′ was unambiguously established using NMR-based conformational analysis. A reaction mechanism was proposed. A test series of novel desosamine-modified 14- and 15-membered macrolides, bearing N′-alkyl-2-imino-1, 3-thiazolidines fused to the desosamine sugar were prepared.
Izvorni jezik
Engleski
Znanstvena područja
Kemija
Citiraj ovu publikaciju:
Časopis indeksira:
- Current Contents Connect (CCC)
- Web of Science Core Collection (WoSCC)
- Science Citation Index Expanded (SCI-EXP)
- SCI-EXP, SSCI i/ili A&HCI
- Scopus
