Please use this identifier to cite or link to this item: https://doi.org/10.1002/chem.200802601
Title: Synthesis of α-stereogenic amides and ketones by enantioselective conjugate addition of 1,4-dicarbonyl but-2-enes
Authors: Jiang, Z. 
Yang, Y.
Pan, Y.
Zhao, Y. 
Liu, H.
Tan, C.-H. 
Keywords: Asymmetric catalysis
Dicarbonyl compounds
Enantiose-lectivity
Organocatalysis
Issue Date: 4-May-2009
Citation: Jiang, Z., Yang, Y., Pan, Y., Zhao, Y., Liu, H., Tan, C.-H. (2009-05-04). Synthesis of α-stereogenic amides and ketones by enantioselective conjugate addition of 1,4-dicarbonyl but-2-enes. Chemistry - A European Journal 15 (19) : 4925-4930. ScholarBank@NUS Repository. https://doi.org/10.1002/chem.200802601
Abstract: In the conjugate addition reaction of a a,|3-unsaturated compound, the new stereogenic center is created in the b-position. In contrast, conjugate addition to 1,4-dicarbonyl but-2-enes will generate an astereogenic center with respect to one of the carbonyl groups, which informally, can be considered as an inversion of normal reactivity patterns or Umpolung. In this paper, we demonstrate that chiral bicy-clic guanidine can catalyze the addition of 1,3-dicarbonyl compounds to 1,4-di-carbonyl but-2-enes [(E)-4-oxo-4-aryl- butenamides and (E)-4-oxo-4-arylbute-nones] with high regioselectivity and enantioselectivity (ee values up to 97%). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Source Title: Chemistry - A European Journal
URI: http://scholarbank.nus.edu.sg/handle/10635/77194
ISSN: 09476539
DOI: 10.1002/chem.200802601
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