From Central to Helical Chirality: Synthesis of  P  and  M  Enantiomers of [5]Helicenequinones and Bisquinones from (S S )‐2‐( p ‐Tolylsulfinyl)‐ 1,4‐benzoquinone | Zendy

Carreño M. Carmen | Zendy; GarcíaCerrada Susana | Zendy; Urbano Antonio | Zendy

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From Central to Helical Chirality: Synthesis of P and M Enantiomers of [5]Helicenequinones and Bisquinones from (S S )‐2‐( p ‐Tolylsulfinyl)‐ 1,4‐benzoquinone

Author(s) -

Carreño M. Carmen,

GarcíaCerrada Susana,

Urbano Antonio

Publication year - 2003

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.200304835

Subject(s) - enantiopure drug , aromatization , helicene , chemistry , enantiomer , sulfoxide , chirality (physics) , stereochemistry , stereospecificity , domino , cycloaddition , medicinal chemistry , enantioselective synthesis , molecule , organic chemistry , catalysis , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark

The reaction of 1,4‐divinyl‐1,3‐cyclohexadiene, 5,8‐dimethoxy‐ or tert‐ butyldimethylsilyloxy‐3‐vinyl‐1,2‐dihydrophenanthrene or 6‐vinyl‐7,8‐dihydro‐1,4‐phenanthrenequinone with an excess of enantiopure (S S )‐2‐( p ‐tolylsulfinyl)‐1,4‐benzoquinone ( 2 ) led to the direct formation of enantioenriched dihydro[5]helicenequinones or bisquinones (50→98 % ee ). A domino Diels–Alder cycloaddition/sulfoxide elimination/partial aromatization process occurs, being the absolute configuration of the final helicene defined in the aromatization step. Both M and P helimers are accessible through a stepwise enantiodivergent process if the pentacyclic dihydroaromatic intermediate resulting in the two first steps is aromatized in the presence of (±)‐ 2 , DDQ, CAN or DBU.

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