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Enantioselective Synthesis of Densely Functionalized Pyranochromenes via an Unpredictable Cascade Michael–Oxa‐Michael–Tautomerization Sequence
Author(s) -
Ren Qiao,
Gao Yaojun,
Wang Jian
Publication year - 2010
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.201002490
Subject(s) - malononitrile , michael reaction , enantioselective synthesis , bifunctional , tautomer , indane , chemistry , nucleophile , thiourea , organic chemistry , combinatorial chemistry , catalysis
A surprising example of enantioselective cascade Michael–oxa‐Michael–tautomerization reactions of malononitrile and benzylidenechromanones has been developed. In this case, malononitrile functions as both nucleophile and electrophile. Meanwhile, a simple bifunctional indane amine–thiourea catalyst has been discovered to promote this process to afford high yields (up to 99%) and high to excellent enantiomeric excesses (81–99% ee ).