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Proline Catalyzed Asymmetric Aldol Reaction between Methyl Ketones and α ‐Ketoesters †
Author(s) -
Wang YaJun,
Shen ZongXuan,
Li Bin,
Zhang YaWen
Publication year - 2006
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200690223
Subject(s) - chemistry , aldol reaction , acetone , steric effects , proline , reactivity (psychology) , butanone , catalysis , selectivity , optically active , aldol condensation , organic chemistry , enantioselective synthesis , ketone , medicinal chemistry , amino acid , biochemistry , medicine , alternative medicine , pathology , solvent
Direct asymmetric aldol additions of acetone/and butanone to α ‐ketoesters were achieved using L ‐proline as a chiral catalyst. Various optically active α ‐hydroxyesters were obtained in the yields of 43%–93% with enantioselectivities up to 81% e . e . The steric effect seems to be an important factor which influences the activity and the selectivity of the reaction. Acetone showed higher reactivity than butanone while the latter provided better enantioselectivity in some cases.