基于二肽的手性叔胺催化的 5H-噻唑/噁唑-4-酮的不对称共轭加成反应。
Dipeptide-Based Chiral Tertiary Amine-Catalyzed Asymmetric Conjugate Addition Reactions of 5H-Thiazol/Oxazol-4-Ones.
机构信息
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University , Kaifeng, Henan 475004, P. R. China.
Division of Chemistry and Biological Chemistry, Nanyang Technological University , 21 Nanyang Link, 637371, Singapore.
出版信息
J Org Chem. 2016 Dec 2;81(23):11916-11923. doi: 10.1021/acs.joc.6b02384. Epub 2016 Nov 15.
Highly enantio- and chemo-selective 1,4-conjugate addition process of 5H-thiazol-4-ones with maleimides or 1,4-naphthoquinones, and 5H-oxazol-4-ones with maleimides were performed under a dipeptide-based tertiary amine (DP-UAA) catalyst. A series of valuable N,S- and N,O-containing heterocyclic compounds with excellent enantio- and disastereo-selectivities (up to >99% ee, > 20:1 dr) were attained.
在基于二肽的叔胺（DP-UAA）催化剂作用下，5H-噻唑-4-酮与马来酰亚胺或 1,4-萘醌、5H-噁唑-4-酮与马来酰亚胺进行高度对映选择性和化学选择性的 1,4-共轭加成反应。得到了一系列具有优异对映选择性和非对映选择性的含 N，S-和 N，O-杂环化合物（高达 >99%ee，>20:1dr）。
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