First asymmetric synthesis of dihydrobenzo[c]phenanthrene-1,4-quinones with helical chirality
- 19 July 2001
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 16,p. 1452-1453
- https://doi.org/10.1039/b103447m
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.Keywords
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