Please use this identifier to cite or link to this item:
|Title:||Synthesis of α-stereogenic amides and ketones by enantioselective conjugate addition of 1,4-dicarbonyl but-2-enes||Authors:||Jiang, Z.
|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.||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/10635/95133||ISSN:||09476539|
|Appears in Collections:||Staff Publications|
Show full item record
Files in This Item:
There are no files associated with this item.
checked on May 18, 2018
WEB OF SCIENCETM
checked on Dec 31, 2018
checked on Jan 26, 2020
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.