Organic Letters
Organic Letters
5 years ago

Asymmetric Benzylic Functionalizations of 3-Vinyl Benzofurans via Cascade Formal Trienamine–Vinylogous Iminium Ion Activation

Asymmetric Benzylic Functionalizations of 3-Vinyl Benzofurans via Cascade Formal Trienamine–Vinylogous Iminium Ion Activation
Ben-Xian Xiao, Ying-Chun Chen, Wei Du, Ru-Jie Yan, Xin-Yue Gao
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02287

DOI: 10.1021/acs.orglett.7b02287

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