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Catalytic Asymmetric Construction of Spiro(γ‐butyrolactam‐γ‐butyrolactone) Moieties through Sequential Reactions of Cyclic Imino Esters with Morita–Baylis–Hillman Bromides
Author(s) -
Teng HuaiLong,
Huang He,
Wang ChunJiang
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201201475
Subject(s) - catalysis , baylis–hillman reaction , chemistry , morita therapy , organic chemistry , medicinal chemistry , mathematics , pure mathematics
Spiro(γ‐butyrolactam‐γ‐butyrolactone) : A route to enantioenriched spiro(γ‐butyrolactam‐γ‐butyrolactone) compounds, a valuable motif for drug discovery, was developed by use of a highly efficient copper(I)/TF‐BiphamPhos‐catalyzed tandem Michael addition–elimination of homoserine lactone derived cyclic imino esters with Morita–Baylis–Hillman (MBH) bromides, followed by treatment with para ‐toluenesulfonic acid (see scheme).