4.7 Article

Unveiling the abnormal effect of temperature on enantioselectivity in the palladium-mediated decabonylative alkylation of MBH acetate

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 18, Pages 5058-5063

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo00782c

Keywords

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Funding

  1. National Natural Science Foundation of China [22078370, 21776318, 22078369, 81703365, 22003077]
  2. Central South University
  3. Nanning Normal University

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In a newly developed palladium-catalysed enantioselective nucleophilic substitution reaction, an unusual temperature-enantioselectivity relationship was observed where higher enantioselectivity was achieved at an abnormally high temperature (140 degrees C) in less than 5 minutes. Experimental and computational studies suggest that temperature-dependent changes in the rate-determining steps may be responsible for the abnormal effect of temperature on stereocontrol in this process.
An unusual temperature-enantioselectivity relationship was observed in the newly developed palladium-catalysed enantioselective nucleophilic substitution of cyclic Morita-Baylis-Hillman acetate and 4,4,4-trifluoro-1-phenyl-1,3-butanedione. In this transformation, higher enantioselectivity was achieved at an abnormally high temperature (140 degrees C) in less than 5 min. Comprehensive experimental and computational studies disclose that temperature-dependent changes in the rate-determining steps might be responsible for the abnormal effect of temperature on stereocontrol in this process.

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