Oxindole‐chromones C3 Synthons Directed Stereocontrolled Construction of Five Contiguous Stereocenters on Spiro[tetrahydrocyclopenta[b]chromanone‐oxindole]s. Issue 23 (22nd October 2019)

• Record Type: Journal Article
• Authors: Xu, Sheng‐Wen; Liu, Xiong‐Wei; Zuo, Xiong; Zhou, Gen; Gong, Yi; Liu, Xiong‐Li; Zhou, Ying
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 23(2019)
• Page Start: 5328
• Page End: 5333
• Publication Date: 2019-10-22
• Subjects: Bifunctional oxindole-chromone C3 synthon -- Organocatalytic cascade cycloaddition reaction -- Five contiguous stereocenters -- Stereoselectivities -- Tetrahydrocyclopenta[b]chromanone; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201901091
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: The first example of bifunctional oxindole‐chromone C3 synthon directed organocatalytic cascade cycloaddition reaction is developed, serving as a fruitful strategy for the facile access of optically active tetrahydrocyclopenta[b]chromanone bearing one spirooxindole with five contiguous stereocenters. All the products are smoothly obtained with up to 83% yield, >20:1 d.r. and >99% ee. This is also the first asymmetric catalytic construction of tetrahydrocyclopenta[b] chromanone and tetrahydrocyclopenta[b]chromanone‐spirooxindole scaffold, thus to facilitate the search for new bioactive entities. Abstract :