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Highly Enantioselective Construction of Spirocyclopentaneoxindoles Containing Four Consecutive Stereocenters through an Organocatalytic Iminium–Enamine Cascade Reaction
Author(s) -
Ding LiangZhong,
Zhong TongSheng,
Wu Hao,
Wang YongMei
Publication year - 2014
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.201402687
Subject(s) - stereocenter , iminium , chemistry , enamine , diastereomer , enantioselective synthesis , organocatalysis , enantiomer , stereochemistry , cascade reaction , cascade , combinatorial chemistry , organic chemistry , catalysis , chromatography
Abstract Spirocyclopentaneoxindole derivatives containing four consecutive stereocenters, including a spiro quaternary center, were constructed by an organocatalytic iminium–enamine cascade sequence in good yields (up to 86 %) with excellent enantiomeric (up to >99 % ee ) and diastereomeric purities (up to >99:1 dr ). This highly efficient procedure will allow diversity‐oriented syntheses of this intriguing class of compounds with potential biological activities.