Copper-Catalyzed Asymmetric Alkylation of β-Keto Esters with Xanthydrols

Authors

  • Paz Trillo,

    1. Departamento de Química Orgánica, Facultad de Ciencias, and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo 99, 03080 Alicante, Spain, Fax: (+34)-96-590-3549; phone: (+34)-96-590-3549
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  • Alejandro Baeza,

    Corresponding author
    1. Departamento de Química Orgánica, Facultad de Ciencias, and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo 99, 03080 Alicante, Spain, Fax: (+34)-96-590-3549; phone: (+34)-96-590-3549
    • Departamento de Química Orgánica, Facultad de Ciencias, and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo 99, 03080 Alicante, Spain, Fax: (+34)-96-590-3549; phone: (+34)-96-590-3549

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  • Carmen Nájera

    Corresponding author
    1. Departamento de Química Orgánica, Facultad de Ciencias, and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo 99, 03080 Alicante, Spain, Fax: (+34)-96-590-3549; phone: (+34)-96-590-3549
    • Departamento de Química Orgánica, Facultad de Ciencias, and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo 99, 03080 Alicante, Spain, Fax: (+34)-96-590-3549; phone: (+34)-96-590-3549

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Abstract

The copper(II) triflate-tert-butyl-bisoxazoline [Cu(OTf)2-t-Bu-BOX]-catalyzed asymmetric alkylation of β-keto esters using free benzylic alcohols such as xanthydrols, as alkylating agents, is herein described for the first time. This green protocol renders in general the corresponding products with good results in terms of both yields and enantioselectivities using different keto esters, even when quaternary stereocenters were created. The scope, limitations and mechanistic aspects of the process are also discussed.

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