First asymmetric synthesis of dihydrobenzo[c]phenanthrene-1,4-quinones with helical chirality

Authors
Carreno, MC Garcia-Cerrada, S Sanz-Cuesta, MJ Urbano, A
Citation
Mc. Carreno et al., First asymmetric synthesis of dihydrobenzo[c]phenanthrene-1,4-quinones with helical chirality, CHEM COMMUN, (16), 2001, pp. 1452-1453
Citations number
27
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
16
Year of publication
2001
Pages
1452 - 1453
Database
ISI
SICI code
1359-7345(20010821):16<1452:FASODW>2.0.ZU;2-J
Abstract
The first enantioselective synthesis of 12-tert-butyl substituted 7,8-dihyd robenzo[c]phenanthrene-1,4-quinones having helical chirality is achieved wi th good chemical and optical yields through a domino Diels-Alder reaction-s ulfoxide elimination-oxidation process starting from enantiopure (S)-2-(p-t otylsulfinyl)-1,4-benzoquinone and 5-tert-butyl substituted 3-vinyl-1,2-dih ydronaphthalenes as dienes.