Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives.
نویسندگان
چکیده
An enantioselective hydroxylative dearomatization of 2-naphthols with oxaziridines has been accomplished using a N,N'-dioxide-scandium(iii) complex catalyst. Various substituted ortho-quinols could be obtained in high yields (up to 99%) and enantioselectivities (up to 95 : 5 er). This methodology could be applied in the synthesis of bioactive lacinilenes in a gram-scale reaction. Based on the experimental investigations and previous work, a possible catalytic model was proposed.
منابع مشابه
Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives† †Electronic supplementary information (ESI) available. CCDC 1536822. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc02809a Click here for additional data file. Click here for additional data file.
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Amidoalkyl-2-naphthols as synthetic intermediates play an important role in medicinal chemistry due to their remarkable biological and many pharmacological properties. Owing to the versatile biological activities, industrial and synthetic applications of these compounds, introduction of an alternative methodology is urgent in synthetic organic chemistry. Low yield and harsh reaction conditions ...
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ورودعنوان ژورنال:
- Chemical science
دوره 8 9 شماره
صفحات -
تاریخ انتشار 2017