Journal
TETRAHEDRON-ASYMMETRY
Volume 25, Issue 9, Pages 697-704Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2014.02.017
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Optically active 2-substituted-1-indanones or 2-substituted-1-tetraiones are isolated from amino alcohol-mediated asymmetric domino reactions of alpha-disubstituted ketones, beta-ketoesters, enol carbonates, alpha, beta-unsaturated ketones, a silyl enol ether, or a beta-ketoacid, with some of these reactions occurring under UV-light irradiation or Pd catalysis. The absence of a relationship between the nature of the substrate and the absolute configuration of the ketone produced is due to the protonation of a common ammonium enolate as the key enantioselective step. The enantioselectivity depends on various factors, which indicates the occurrence of side pathways. (C) 2014 Elsevier Ltd. All rights reserved.
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