钯催化的氨基磺酸亚胺衍生的氮杂二烯的(3 + 2)和(4 + 2)环加成反应：螺环吡咯烷和四氢喹啉的合成
Palladium-Catalyzed (3+2) and (4+2) Cycloaddition Reactions of Sulfamidate Imine-Derived Azadienes: Synthesis of Spirocyclic Pyrrolidines and Tetrahydroquinolines.
作者信息
Chao Chi Bong Eric, Pham Quoc Hoang, Richardson Christopher, Pyne Stephen G, Hyland Christopher J T
机构信息
School of Chemistry and Molecular Bioscience, Molecular Horizons Research Institute, University of Wollongong, Northfields Avenue, Wollongong, New South Wales 2522, Australia.
出版信息
J Org Chem. 2024 Sep 20;89(18):13744-13755. doi: 10.1021/acs.joc.4c01425. Epub 2024 Aug 29.
Diastereoselective Pd-catalyzed (3+2) and (4+2) cycloaddition reactions of sulfamidate imine-derived 1-azadienes with zwitterionic N-dipoles derived from 1-tosyl-2-vinylaziridine and 4-vinylbenzoxazinone have been developed. These reactions provide highly functionalized azaspirocycles featuring three contiguous stereocenters. The sulfonyl imine moiety of the cycloadducts can be fully reduced to access valuable β-amino alcohols.
已开发出由氨基磺酸亚胺衍生的1-氮杂二烯与由1-对甲苯磺酰基-2-乙烯基氮丙啶和4-乙烯基苯并恶嗪酮衍生的两性离子N-偶极子的非对映选择性钯催化(3+2)和(4+2)环加成反应。这些反应提供了具有三个相邻立体中心的高度官能化氮杂螺环。环加成产物的磺酰亚胺部分可被完全还原以得到有价值的β-氨基醇。
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