کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5220783 1383399 2011 7 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Asymmetric synthesis of multi-substituted spiro[5,5]undecane-1,5,9-triones via organocatalytic three-component reaction
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Asymmetric synthesis of multi-substituted spiro[5,5]undecane-1,5,9-triones via organocatalytic three-component reaction
چکیده انگلیسی

The asymmetric domino three-component Knoevanagel-Diels-Alder addition (ATCDA) reaction, as an important methodology, has been utilized to construct complex product from ordinary starting materials. In this report, many typical organoamine catalysts were investigated to achieve highly efficient asymmetric three-component reaction of enones 2, aldehydes 3 and Meldrum's acid 4. Various pharmacological multi-substituted spiro[5,5]undecane-1,5,9-triones promoted by 9-amino-9-deoxy-epi-quinine 1 g in one-pot, were obtained in moderate to good yields (up to 81%) with excellent diastereo-(>99:1 dr) and enantioselectivities (up to 97% ee). Meanwhile, based on the controlled experiments and analytical data, a reasonable mechanism of dual-activity for this reaction has been proposed.

The asymmetric domino three-component Knoevanagel-Diels-Alder addition (ATCDA) reaction, as an important methodology, has been utilized to construct complex product from ordinary starting materials. In this report, many typical organoamine catalysts were investigated to achieve highly efficient asymmetric three-component reaction of enones 2, aldehydes 3 and Meldrum's acid 4. Various pharmacological multi-substituted spiro[5,5]undecane-1,5,9-triones promoted by 9-amino-9-deoxy-epi-quinine 1 g in one-pot, were obtained in moderate to good yields (up to 81%) with excellent diastereo-(>99:1 dr) and enantioselectivities (up to 97% ee). Meanwhile, based on the controlled experiments and analytical data, a reasonable mechanism of dual-activity for this reaction has been proposed.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 67, Issue 10, 11 March 2011, Pages 1781-1787
نویسندگان
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