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Issue 50, 2016
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Catalyst-controlled switch of regioselectivity in the asymmetric allylic alkylation of oxazolones with MBHCs

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Abstract

A catalyst-controlled switch of regioselectivity in asymmetric allylic alkylation of oxazolones with MBHCs was described. The SN2′–SN2′ reaction catalysed by a quinine-derived base produced γ-selective secondary allylic oxazolone derivatives, whereas the addition–elimination reaction catalysed by an amino acid-derived bifunctional urea catalyst provided β-selective primary adducts.

Graphical abstract: Catalyst-controlled switch of regioselectivity in the asymmetric allylic alkylation of oxazolones with MBHCs

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Publication details

The article was received on 18 Apr 2016, accepted on 19 May 2016 and first published on 19 May 2016


Article type: Communication
DOI: 10.1039/C6CC03246J
Chem. Commun., 2016,52, 7882-7885

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    Catalyst-controlled switch of regioselectivity in the asymmetric allylic alkylation of oxazolones with MBHCs

    G. Zhu, J. Yang, G. Bao, M. Zhang, J. Li, Y. Li, W. Sun, L. Hong and R. Wang, Chem. Commun., 2016, 52, 7882
    DOI: 10.1039/C6CC03246J

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