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N ‐Heterocyclic Carbene‐Catalyzed Homoenolate Additions with N ‐Aryl Ketimines as Electrophiles: Efficient Synthesis of Spirocyclic γ‐Lactam Oxindoles
Author(s) -
Zhang Bo,
Feng Peng,
Sun LiHui,
Cui Yuxin,
Ye Song,
Jiao Ning
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201201375
Subject(s) - umpolung , carbene , electrophile , aryl , catalysis , chemistry , lactam , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , alkyl , nucleophile
In pole position : A simple and efficient approach to spirocyclic γ‐lactam oxindoles by the N ‐heterocyclic carbene catalyzed addition of homoenloate equivalents to N ‐aryl isatinimines has been developed (see scheme). The use of N ‐aryl isatinimines as electrophiles in the NHC‐catalyzed umpolung reaction of α,β‐unsaturated aldehydes is demonstrated for the first time.