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Issue 9, 2011
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Multifunctional chiral phosphines-catalyzed highly diastereoselective and enantioselective substitution of Morita–Baylis–Hillman adducts with oxazolones

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Abstract

Multifunctional chiral phosphine (phosphine–thiourea type) L2-catalyzed allylic substitutions of MBH adducts 1 with oxazolones 2 produce the corresponding optically active adducts 3 in good to excellent yields and ee's as well as moderate to good de's under mild conditions. The synergistic interaction between hydrogen bond donor site and nucleophilic site has been discussed, indicating that finely tuning the active sites of the multifunctional phosphine organocatalysts is very important.

Graphical abstract: Multifunctional chiral phosphines-catalyzed highly diastereoselective and enantioselective substitution of Morita–Baylis–Hillman adducts with oxazolones

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Publication details

The article was received on 05 Jan 2011, accepted on 11 Feb 2011 and first published on 14 Feb 2011


Article type: Paper
DOI: 10.1039/C1OB00017A
Org. Biomol. Chem., 2011,9, 3349-3358

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    Multifunctional chiral phosphines-catalyzed highly diastereoselective and enantioselective substitution of Morita–Baylis–Hillman adducts with oxazolones

    Y. Yang, C. Pei and M. Shi, Org. Biomol. Chem., 2011, 9, 3349
    DOI: 10.1039/C1OB00017A

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