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Issue 3, 2017
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Unusual reversal of enantioselectivity in the asymmetric autocatalysis of pyrimidyl alkanol triggered by chiral aromatic alkanols and amines

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Abstract

Temperature dependent inversion of enantioselectivity in asymmetric catalysis is an interesting and somewhat unusual phenomenon. We have observed temperature dependent inversion of enantioselectivity in the asymmetric autocatalysis reaction when triggered by a wide scope of enantioenriched alcohols and amines. The addition reaction of diisopropylzinc to pyrimidine-5-carbaldehyde in the presence of enantiopure alcohols or amines affords the pyrimidyl alkanol product at 0 °C with high ee. However, lowering the reaction temperature to −44 °C affords the opposite enantioselectivity.

Graphical abstract: Unusual reversal of enantioselectivity in the asymmetric autocatalysis of pyrimidyl alkanol triggered by chiral aromatic alkanols and amines

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Publication details

The article was received on 06 Nov 2016, accepted on 02 Dec 2016 and first published on 02 Dec 2016


Article type: Communication
DOI: 10.1039/C6OB02415G
Citation: Org. Biomol. Chem., 2017,15, 555-558
  • Open access: Creative Commons BY-NC license
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    Unusual reversal of enantioselectivity in the asymmetric autocatalysis of pyrimidyl alkanol triggered by chiral aromatic alkanols and amines

    A. Matusmoto, S. Fujiwara, Y. Hiyoshi, K. Zawatzky, A. A. Makarov, C. J. Welch and K. Soai, Org. Biomol. Chem., 2017, 15, 555
    DOI: 10.1039/C6OB02415G

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