Catalytic Asymmetric Direct Vinylogous Michael Addition of Deconjugated Butenolides to Maleimides for the Construction of Quaternary Stereogenic Centers

Authors

  • Madhu Sudan Manna,

    1. Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012 (India), Fax: (+91) 8023600529
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  • Prof. Dr. Santanu Mukherjee

    Corresponding author
    1. Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012 (India), Fax: (+91) 8023600529
    • Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012 (India), Fax: (+91) 8023600529
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Abstract

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Competition under control: A practical and efficient direct asymmetric vinylogous Michael reaction of deconjugated butenolides has been developed (see scheme). The products of this reaction, highly functionalized chiral succinimides, are obtained in excellent yield with high diastereoselectivity (up to d.r.=18:1) and outstanding enantioselectivity (up to e.r.=99.5:0.5).

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