Asymmetric Benzylic Functionalizations of 3-Vinyl Benzofurans via Cascade Formal Trienamine-Vinylogous Iminium Ion Activation.
Org Lett
; 19(17): 4652-4655, 2017 09 01.
Article
em En
| MEDLINE
| ID: mdl-28825488
ABSTRACT
An efficient approach to construct chiral 1,1-disubstituted ethane derivatives is presented. This strategy relies on the formation of the key dearomatizative vinylogous iminium ion species through protonation of the formal trienamine intermediates between 2-(3-vinylbenzofuran-2-yl)ethan-1-ones and a chiral primary amine. An array of nucleophiles, including 4-hydroxycoumarins, indoles, etc., have been effectively assembled at the benzylic site, delivering the expected 1,1-disubstituted ethane products in moderate to excellent enantioselectivity.
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MEDLINE
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En
Ano de publicação:
2017
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Article