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Enantioselective Synthesis of CF 3 ‐Containing 3,2’‐Pyrrolidinyl Spirooxindoles and Dispirooxindoles via Thiourea‐Catalyzed Domino Michael/Mannich [3+2] Cycloaddition Reactions
Author(s) -
Lin Ye,
Song YongXing,
Du DaMing
Publication year - 2019
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.201801608
Subject(s) - stereocenter , chemistry , thiourea , enantioselective synthesis , domino , cycloaddition , catalysis , vicinal , michael reaction , yield (engineering) , organocatalysis , mannich reaction , organic chemistry , medicinal chemistry , combinatorial chemistry , materials science , metallurgy
An efficient and practical organocatalytic asymmetric domino Michael/Mannich [3+2] cycloaddition of N ‐2,2,2‐trifluoroethylisatin ketimines and arylidene azlactones by using a hydroquinine‐derived thiourea as the catalyst has been disclosed. Under mild conditions, a broad range of CF 3 ‐containing 3,2’‐pyrrolidinyl spirooxindole/ dispirooxindole derivatives bearing four adjacent stereogenic centers including two vicinal spiro quaternary chiral centers were obtained in high yields (up to 99% yield) with excellent diastereoselectivities (>20:1 dr , in all case) and enantioselectivities (up to >99% ee ).