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Asymmetric Organocatalytic Quadruple Cascade Reaction of 2‐Hydroxychalcone with Cinnamaldehyde for the Construction of Tetrahydro‐6 H ‐benzo[ c ]chromene Containing Five Stereocenters
Author(s) -
Liu Lingyan,
Zhu Yunna,
Huang Kaimeng,
Wang Bing,
Chang Weixing,
Li Jing
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.201402159
Subject(s) - chemistry , stereocenter , michael reaction , cinnamaldehyde , adduct , steric effects , cascade reaction , aldol condensation , aldol reaction , stereochemistry , enantioselective synthesis , organic chemistry , catalysis
An asymmetric organocatalytic quadruple cascade reaction was developed for the stable and sterically hindered 2‐hydroxychalcones and substituted cinnamaldehydes. This process proceeded through an oxa‐Michael–Michael–Michael–aldol condensation to afford highly functionalized tetrahydro‐6 H ‐benzo[ c ]chromene derivatives with high diastereoselectivity and enantioselectivity (>99 % ee ). The structure of adduct 4g with five stereocenters was unambiguously confirmed by single‐crystal X‐ray diffraction, and valuable mass spectrometry data provided direct support for the proposed reaction mechanism.