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Asymmetric syn ‐Aldol Reaction of α‐Hydroxy Ketones with Tertiary Amine Catalysts
Author(s) -
Baś Sebastian,
Woźniak Łukasz,
Cygan Judyta,
Mlynarski Jacek
Publication year - 2013
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.201300872
Subject(s) - aldol reaction , chemistry , enamine , cinchonine , catalysis , tertiary amine , amine gas treating , organic chemistry , asymmetric induction , enantioselective synthesis , organocatalysis
The tertiary amine‐catalyzed direct asymmetric aldol reaction of 2‐hydroxyacetophenones (2‐hydroxy‐1‐arylethanones) with a variety of aliphatic aldehydes has been demonstrated. By using 20 mol‐% of unmodified cinchonine as catalyst, the direct aldol reaction products were isolated in good yields and with remarkably high syn diastereocontrol and good asymmetric induction (40–78 % ee ). This newly elaborated tertiary‐amine‐catalyzed direct asymmetric aldol reaction has extended the scope of organocatalytic processes to aromatic α‐hydroxy ketones, which have hitherto been unreactive towards enamine catalysis.