Catalytic Asymmetric Synthesis of Axially and Centrally Chiral 1,2-Dihydrobenzofuro[3,2-b]pyridines through a [2 + 2]
Wanlong Xiao1, Fang Li1, Xiaohua Liu1
1Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
Abstract:
A catalytic asymmetric tandem cyclization of azadienes and ortho-alkynylnaphthols accelerated by the chiral N,N'-dioxide-gadolinium(III) complex is disclosed. This method allows the synthesis of a range of 1,2-dihydrobenzofuro[3,2-b]pyridines containing both axially and centrally chiral elements in high yields and excellent stereoselectivities (up to >99% yield, 91:9 dr, 98% ee). A control experiment revealed that this process proceeded through a multistep [2 + 2] cycloaddition/retroelectrocyclization/tautomerism/1,6-conjugate addition cascade.
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