Premium
Organocatalytic Enantioselective Cascade Aza‐Michael/Michael Addition Sequence for Asymmetric Synthesis of Chiral Spiro[pyrrolidine‐3,3′‐oxindole]s
Author(s) -
Zhao BoLiang,
Du DaMing
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500306
Subject(s) - pyrrolidine , oxindole , stereocenter , squaramide , enantioselective synthesis , michael reaction , chemistry , organocatalysis , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
The spiro[pyrrolidine‐3,3′‐oxindole] scaffold is common to a range of bioactive compounds; however, the asymmetric synthesis of this scaffold is complicated due to the presence of multiple chiral centers. An organocatalytic asymmetric cascade aza‐Michael/Michael addition between tosylaminomethyl enones or enoates and 3‐ylideneoxindoles catalyzed by a chiral squaramide that afforded complex and flexible spiro[pyrrolidine‐3,3’‐oxindole]s has been developed. Single‐step construction of molecules with three contiguous stereocenters including one quaternary center in excellent yields with highly diastereo‐ and enantioselectivity are rare and should be useful in medicinal chemistry and diversity oriented synthesis of this intriguing class of compounds.