Xiao Wanlong, Li Fang, Liu Xiaohua, Cao Weidi, Feng Xiaoming
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
Org Lett. 2023 Nov 10;25(44):8005-8009. doi: 10.1021/acs.orglett.3c03183. Epub 2023 Oct 31.
A catalytic asymmetric tandem cyclization of azadienes and -alkynylnaphthols accelerated by the chiral ,'-dioxide-gadolinium(III) complex is disclosed. This method allows the synthesis of a range of 1,2-dihydrobenzofuro[3,2-]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.
公开了一种由手性双二氧化物-钆(III)配合物加速的氮杂二烯与-炔基萘酚的催化不对称串联环化反应。该方法能够以高收率和优异的立体选择性（产率高达>99%，非对映体比例为91:9，对映体过量值为98%）合成一系列同时含有轴手性和中心手性元素的1,2-二氢苯并呋喃并[3,2 -]吡啶。对照实验表明，该过程通过多步[2 + 2]环加成/逆电环化/互变异构/1,6-共轭加成串联反应进行。
