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Enantioselective Cascade Reaction of α‐Cyano Ketones and Isatylidene Malononitriles: Asymmetric Construction of Spiro[4 H ‐pyran‐oxindoles]
Author(s) -
Xie Jin,
Xing WeiLong,
Sha Feng,
Wu XinYan
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600432
Subject(s) - oxindole , chemistry , enantioselective synthesis , pyran , organocatalysis , catalysis , cascade , organic chemistry , combinatorial chemistry , chromatography
α‐Cyano ketones have been employed for the first time as Michael donors in the construction of chiral spiro compounds. By using only 2 mol‐% of a chiral multifunctional organocatalyst, chiral spiro[4 H ‐pyran‐oxindole] derivatives were prepared in yields of 97–99 % with enantioselectivities of 76–97 % ee . This method provides a new approach to the synthesis of chiral spirocyclic oxindoles.