Kanchupalli Vinaykumar, Katukojvala Sreenivas
Department of Chemistry, Indian Institute of Science Education & Research BhopaI, Madhya, Pradesh, 462066, India.
Angew Chem Int Ed Engl. 2018 May 4;57(19):5433-5437. doi: 10.1002/anie.201801976. Epub 2018 Apr 6.
A dirhodium carboxylate catalyzed [1+1+3] annulation reaction of diazoenals and vinyl azides that gives synthetically important enal-functionalized 1-pyrroline derivatives was developed. The reaction involves a novel rhodium-catalyzed olefination of diazoenals with vinyl azides via electrophilic enal carbenoids, resulting in a new class of enal acrylates. The annulation reaction was used for the direct synthesis of valuable deuterated 1-pyrrolines. Structural diversification of the enal-functionalized 1-pyrrolines resulted in the biologically important pyrrolidine-fused oxaziridine, amino acid derivatives, and a 6-azabicyclo[3.2.1]octane motif present in polycyclic alkaloids.
开发了一种由二铑羧酸盐催化的重氮烯醛与乙烯基叠氮化物的[1+1+3]环化反应，该反应能生成具有重要合成价值的烯醛官能化1-吡咯啉衍生物。该反应涉及一种新型的铑催化重氮烯醛与乙烯基叠氮化物通过亲电烯醛类卡宾进行的烯基化反应，生成了一类新型的烯醛丙烯酸酯。该环化反应被用于直接合成有价值的氘代1-吡咯啉。烯醛官能化1-吡咯啉的结构多样化产生了具有生物学重要性的吡咯烷稠合恶唑烷、氨基酸衍生物以及多环生物碱中存在的6-氮杂双环[3.2.1]辛烷结构单元。
