Synthesis of chiral chromenes from levoglucosenone | Sciact - научная деятельность

Synthesis of chiral chromenes from levoglucosenone Научная публикация

Журнал

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Вых. Данные

Год: 2013, Том: 62, Номер: 10, Страницы: 2196-2201 Страниц : 6 DOI: 10.1007/s11172-013-0318-4

Авторы

Samet A.V. ¹ , Lutov D.N. ¹ , Firgang S.I. ¹ , Nelyubina Yu.V. ² , Semenov V.V. ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation

Levoglucosenone, an optically active α,β-unsaturated ketone available from cellulose, undergoes a stereoselective oxa-Michael-aldol domino reaction with 2-hydroxybenzaldehydes with the formation of optically active oxepino[4,5-b]chromen-1-ones. These compounds attacked by nucleophiles undergo recyclization to 4-substituted oxepino[3,4-b]chromen-11a-ols, while their oximes treated with SOCl2 are converted to 3-cyano-2H-chromenes through the Beckmann fragmentation.

Samet A.V. , Lutov D.N. , Firgang S.I. , Nelyubina Y.V. , Semenov V.V.
Synthesis of chiral chromenes from levoglucosenone
Russian Chemical Bulletin. 2013. V.62. N10. P.2196-2201. DOI: 10.1007/s11172-013-0318-4 WOS Scopus OpenAlex

Web of science:	WOS:000339728300012
Scopus:	2-s2.0-84906855937
OpenAlex:	W2081930599

БД	Цитирований
OpenAlex	4
Scopus	4
Web of science	4