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Unusual Ligand‐to‐Metal‐Ratio‐Controlled Bidirectional Enantioselectivity in Pd‐Catalysed [3+3]‐Annulation of Morita–Baylis–Hillman Acetate
Author(s) -
Li Jun,
Wang ShaSha,
Xia PengJu,
Zhao QingLan,
Xiao JunAn,
Xiang HaoYue,
Chen XiaoQing,
Yang Hua
Publication year - 2017
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.201701315
Subject(s) - annulation , chemistry , ligand (biochemistry) , palladium , stereochemistry , enantioselective synthesis , medicinal chemistry , metal , combinatorial chemistry , organic chemistry , catalysis , receptor , biochemistry
An unusual ligand‐to‐palladium‐ratio‐dependent reversal of enantioselectivity was systematically observed in the asymmetric Pd‐catalysed [3+3]‐annulation of Morita–Baylis–Hillman acetate with 4‐hydroxycoumarin or 1,3‐cyclohexanedione. The absolute configurations of the annulation products can be readily inverted by simply modifying the L/Pd ratio from 1:3 to 2:1.
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