期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 349, 期 4-5, 页码 583-594出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200600570
关键词
chiral binaphthyls; configuration determination; naphthopyrones; nigerone; oxidative coupling; quantum chemical circular dichroism calculations
An enantioselective synthesis of the chiral bisnaphthopyrone natural product nigerone and its enantiomer. ent-nigerone, has been realized. The use of constrained 2-naphthol substrates was critical to producing highly functionalized chiral 1,1'-binaphthols via asymmetric oxidative biaryl coupling with 1,5-diaza-cis-decalin copper complexes. The final natural product was formed via a key eight-step isomerization process of the coupling product, bisisonigerone, and proceeded with retention of the biaryl configuration. The axial configurations of bisisonigerone and nigerone were definitively established by a combination of circular dichroism (CD) measurements and quantum chemical CD calculations.
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