Asymmetric Vinylogous Aldol Reaction of  α ‐ketoesters with 3‐alkylidene oxindoles | Zendy

Kumar Krishna | Zendy; Jaiswal Manish K. | Zendy; Singh Ravi P. | Zendy

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Asymmetric Vinylogous Aldol Reaction of α ‐ketoesters with 3‐alkylidene oxindoles

Author(s) -

Kumar Krishna,

Jaiswal Manish K.,

Singh Ravi P.

Publication year - 2017

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201700758

Subject(s) - chemistry , cinchona , enantioselective synthesis , aldol reaction , bifunctional , nucleophile , electrophile , yield (engineering) , thiourea , catalysis , organocatalysis , organic chemistry , stereochemistry , medicinal chemistry , materials science , metallurgy

An efficient enantioselective vinylogous aldol reaction of 3‐alkylidene oxindoles with α ‐ketoesters by a bifunctional thiourea catalyst derived from cinchona alkaloid has been disclosed here. The simultaneous H‐bond directing dual activation of vinylogous nucleophile and electrophile afforded high yield (upto 92%) while obtaining excellent stereocontrol (upto 99% ee).

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