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Asymmetric Aldol Reaction of 3‐Acetyl‐2 H ‐chromen‐2‐ones and Isatins Catalyzed by a Bifunctional Quinidine Urea Catalyst
Author(s) -
Abbaraju Santhi,
Zhao John CongGui
Publication year - 2014
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.201300623
Subject(s) - chemistry , bifunctional , catalysis , aldol reaction , isomerization , moiety , diastereomer , isatin , urea , medicinal chemistry , substrate (aquarium) , organic chemistry , bifunctional catalyst , oceanography , geology
Abstract The asymmetric aldol reaction of 3‐acetyl‐2 H ‐chromen‐2‐ones and isatins has been realized by using a bifunctional quinidine‐derived urea as the catalyst. The corresponding 3‐hydroxyoxindole derivatives containing a 2 H ‐chromen‐2‐one moiety were obtained in good yields and high enantioselectivities. When ( Z )‐ethyl 2‐benzylideneacetoacetate was used as the substrate, a mixture of two diastereomers (both Z and E ) was obtained due to isomerization of the double bond under the reaction conditions.