Hayashi Yujiro, Suga Yurina, Umekubo Nariyoshi
Department of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aramaki Aza-Aoba, Aoba-ku, Sendai, Miyagi 980-8578, Japan.
Org Lett. 2020 Nov 6;22(21):8603-8607. doi: 10.1021/acs.orglett.0c03190. Epub 2020 Oct 19.
An asymmetric domino reaction combining vinylogous Michael reaction, hydration of aldehyde, and oxy-Michael reaction proceeds with α,β-unsaturated aldehydes and α-acyl α,β-unsaturated cyclic ketones in the presence of diphenylprolinol silyl ether to afford tetrahydrochromane derivatives with excellent enantioselectivity. After the domino reaction, addition of Wittig reagent and acid in the same reaction vessel promoted a second domino reaction incorporating retro oxy-Michael reaction, isomerization, and Wittig reaction to afford chiral functionalized cyclic 1,3-diene derivatives with excellent enantioselectivity. Overall, six reaction steps proceed in a one-pot procedure.
一种将乙烯基迈克尔反应、醛的水合反应和氧杂迈克尔反应相结合的不对称多米诺反应，在二苯基脯氨醇硅醚存在下，与α,β-不饱和醛和α-酰基α,β-不饱和环酮发生反应，以优异的对映选择性得到四氢色满衍生物。在多米诺反应之后，在同一反应容器中加入维蒂希试剂和酸，促进了包含逆氧杂迈克尔反应、异构化和维蒂希反应的第二次多米诺反应，以优异的对映选择性得到手性官能化的环状1,3-二烯衍生物。总体而言，六个反应步骤在一锅法中进行。
