Stereoselective Construction of Complex Spirooxindoles via Bisthiourea Catalyzed Three‐Component Reactions1. Issue 12 (17th October 2018)

• Record Type: Journal Article
• Authors: Zhang, Lin‐Lin; Zhang, Ji‐Wei; Xiang, Shao‐Hua; Guo, Zhen; Tan, Bin
• Is Part Of: Chinese journal of chemistry. Volume 36:Issue 12(2018)
• Page Start: 1182
• Page End: 1186
• Publication Date: 2018-10-17
• Subjects: multicomponent reactions -- asymmetric catalysis -- bisthiourea -- Diels‐Alder reaction -- ene‐reaction -- complex spirooxindoles; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.201800368
• Languages: English
• ISSNs: 1001-604X

Abstract

Abstract: A well‐designed three‐component reaction was developed to construct a class of optically active carbazolespirooxindole‐urazoles in good yields with excellent stereoselectivities via tandem Diels‐Alder reaction and ene‐reaction. The driving force originating from aromatization with in situ generated carbazolespirooxindole and the high reactivity of 4‐phenyl‐3 H ‐1, 2, 4‐triazole‐3, 5‐dione facilitate the ene‐reaction in mild conditions. Control experiments indicated that the excellent stereoselectivities of ene‐reaction most likely came from the spatial configuration of the carbazolespirooxindole. The obtained products could be converted to other synthetic useful structures via diverse functionalization. Abstract : A well‐designed three‐component reaction was developed to construct a class of optically active carbazolespirooxindole‐urazoles in good yields with excellent stereoselectivities via tandem Diels‐Alder reaction and ene‐reaction.