Developing reactions to generate complex and modular building blocks in a concise and direct fashion remains a contemporary synthetic challenge. This work describes a stereoselective cascade reaction between allylic azides and acrylates that directly generates tetrahydro-pyrrolo-pyrazole ring systems. These products contain up to four contiguous stereocenters, two of which may be tetrasubstituted carbon atoms attached to a nitrogen atom. Over 30 examples are provided with an average isolated yield of 71% (ranging from 40% to 94%). The reaction was easily scaled to use more than one gram of starting material, and the products can be readily diversified.
Developing reactions to generate complex and modular building blocks in a concise and direct fashion remains a contemporary synthetic challenge. This work describes a stereoselective cascade reaction between allylic azides and n class="Chemical">acrylates that directly generates tetrahydro-pyrrolo-pyrazole ring systems. These products contain up to four contiguous stereocenters, two of which may be tetrasubstituted carbon atoms attached to a nitrogen atom. Over 30 examples are provided with an average isolated yield of 71% (ranging from 40% to 94%). The reaction was easily scaled to use more than one gram of starting material, and the products can be readily diversified.
Authors: Sean M Smith; Gia L Hoang; Rhitankar Pal; Mohammad O Bani Khaled; Liberty S W Pelter; Xiao Cheng Zeng; James M Takacs Journal: Chem Commun (Camb) Date: 2012-12-28 Impact factor: 6.222
Authors: AbdElAziz A Nayl; Ashraf A Aly; Wael A A Arafa; Ismail M Ahmed; Ahmed I Abd-Elhamid; Esmail M El-Fakharany; Mohamed A Abdelgawad; Hendawy N Tawfeek; Stefan Bräse Journal: Molecules Date: 2022-06-09 Impact factor: 4.927