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Enantioselective Synthesis of Spirocyclic Oxindole‐β‐lactones via N‐Heterocyclic Carbene‐Catalyzed Cycloaddition of Ketenes and Isatins
Author(s) -
Wang XiaoNa,
Zhang YanYong,
Ye Song
Publication year - 2010
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.201000187
Subject(s) - chemistry , oxindole , cycloaddition , enantioselective synthesis , carbene , catalysis , decarboxylation , organic chemistry , reagent , ring (chemistry) , combinatorial chemistry , medicinal chemistry
Chiral N‐heterocyclic carbenes were found to be efficient catalysts for the formal [2+2] cycloaddition reaction of disubstituted ketenes and isatins to give the corresponding spirocyclic oxindole‐β‐lactones in good yields with good diastereoselectivities and excellent enantioselectivities. Ring opening with Grignard reagents or decarboxylation of the oxindole spirocyclic‐β‐lactone gave the corresponding 3‐hydroxy‐ or 3‐alkylenyloxindoles in good yields.