Kondoh Azusa, Kato Takuro, Chen Hao, Terada Masahiro
Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan.
Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan.
Org Lett. 2024 Aug 2;26(30):6523-6528. doi: 10.1021/acs.orglett.4c02532. Epub 2024 Jul 19.
An enantioselective addition reaction of alkynyl esters with imines was developed under asymmetric autotandem catalysis with a chiral Brønsted base. A chiral bis(guanidino)iminophosphorane organosuperbase, which has much higher basicity than that of conventional chiral organic bases, efficiently promoted both the intramolecular cyclization for the construction of a benzofuran ring or a benzothiophene ring and the sequential enantioselective direct Mannich-type reaction of diarylmethane derivatives, affording enantio-enriched diarylalkane derivatives that are otherwise difficult to access.
在手性布朗斯特碱的不对称自动串联催化下，开发了一种炔基酯与亚胺的对映选择性加成反应。一种手性双（胍基）亚氨基膦烷有机超强碱，其碱性比传统手性有机碱高得多，能有效促进构建苯并呋喃环或苯并噻吩环的分子内环化反应以及二芳基甲烷衍生物的顺序对映选择性直接曼尼希型反应，得到对映体富集的二芳基烷烃衍生物，而这些衍生物用其他方法难以获得。
