Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 35, Pages 5690-5694Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202000835
Keywords
Asymmetric synthesis; Vinylogous Michael addition; 3-Alkylidene-2-oxindoles; beta,gamma-Unsaturated alpha-keto esters; Michael adduct
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Funding
- DST-India [EMR/2017/000319]
- CSIR [02(0254)/16/EMR-II]
- DAE [201804BRE02RP04978-BRNS]
- CSIR, New Delhi, India
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A highly enantioselective vinylogous Michael addition of 3-alkylidene-2-oxindoles with beta,gamma-unsaturated alpha-keto esters using a bifunctional tertiary-amine thiourea catalyst is demontsrated. The challenging Michael reaction with the beta,gamma-unsaturated alpha-keto esters has been accomplished due to the synchronized H-bond guided dual activation of vinylogous nucleophile and electrophile by catalyst. The reaction afforded product in high yield while resulting in excellent stereocontrol (> 19:1E/Zand upto 99 %ee).
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