First asymmetric synthesis of dihydrobenzo [c] phenanthrene-1, 4-quinones with helical chiralityElectronic supplementary information (ESI) available: experimental …

…, S García-Cerrada, MJ Sanz-Cuesta…

Index: Carreno; Garcia-Cerrada; Sanz-Cuesta; Urbano Chemical Communications, 2001 , # 16 p. 1452 - 1453

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Abstract

The first enantioselective synthesis of 12-tert-butyl substituted 7, 8-dihydrobenzo [c] phenanthrene-1, 4-quinones having helical chirality is achieved with good chemical and optical yields through a domino Diels–Alder reaction–sulfoxide elimination–oxidation process starting from enantiopure (S)-2-(p-tolylsulfinyl)-1, 4-benzoquinone and 5-tert-butyl substituted 3-vinyl-1, 2-dihydronaphthalenes as dienes.