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Organocatalytic Enantioselective Formal Conjugate Addition of a Hydroxymoyl Anion to α,β‐Unsaturated Aldehydes
Author(s) -
Alonso Beatriz,
Reyes Efraím,
Carrillo Luisa,
Vicario Jose L.,
Badía Dolores
Publication year - 2011
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.201100605
Subject(s) - moiety , iminium , enantioselective synthesis , oxime , conjugate , chemistry , michael reaction , combinatorial chemistry , catalysis , computer science , organic chemistry , mathematics , mathematical analysis
Umpoled oxime source : N ‐Nitromethylphthalimide is an excellent hydroxymetanimidoyl anion equivalent; under iminium catalysis and optimized reaction conditions, it undergoes a clean and highly enantioselective Michael addition to enals (see scheme). The nitro(phthalimido)methyl moiety can be then directly converted into an oxime moiety by a simple and high‐yielding protocol.
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