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A Morita–Baylis–Hillman Pathway to Wittig Products: One‐Pot Transformation of Nitroalkylideneoxindoles to Oxindolylidene‐Carboxylates
Author(s) -
Satham Lakshminarayana,
Sankara Chenikkayala Siva,
Namboothiri Irishi N. N.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000852
Subject(s) - chemistry , wittig reaction , isatin , stereoselectivity , reactivity (psychology) , stereochemistry , transformation (genetics) , organic chemistry , catalysis , biochemistry , medicine , alternative medicine , pathology , gene
An unusual Morita–Baylis–Hillman (MBH) type reactivity of isatin‐derived nitroalkenes with activated carbonyl compounds has been demonstrated for the first time. The unexpected 3‐alkylideneoxindole esters were formed in moderate to excellent yields with complete stereoselectivity (only E ‐isomer). The proposed mechanism based on control experiments involves a hybrid MBH–Wittig pathway.