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Palladium‐Catalyzed Bis‐Functionalization of Isatylidenes: A Facile Route towards Spiro‐Indol‐2‐ones
Author(s) -
George Sholly Clair,
John Jubi,
Anas Saithalavi,
John Joshni,
Yamamoto Yoshinori,
Suresh Eringathodi,
Radhakrishnan K. V.
Publication year - 2010
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.201000604
Subject(s) - chemistry , palladium , catalysis , metathesis , ring closing metathesis , cyclohexene , surface modification , amphiphile , combinatorial chemistry , salt metathesis reaction , ring (chemistry) , organic chemistry , polymerization , copolymer , polymer
An effective protocol has been developed for the construction of 3,3‐disubstituted indol‐2‐ones from isatylidenes by utilizing amphiphilic bis‐π‐allylpalladium and related intermediates. The developed strategy is a new method for the quaternization of position 3 of the indol‐2‐one towards disubstituted functionalized indol‐2‐ones. These products were subjected to ring‐closing metathesis towards the synthesis of spiro[cyclohexene‐1,3′‐indol]‐2′‐ones and spiro[oxep‐5‐ene‐2,3′‐indol]‐2′‐ones, which are of biological interest.