Abstract
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.
Recommended Citation
A. S. Carlson et al., "A Cascade Reaction Of Cinnamyl Azides With Acrylates Directly Generates Tetrahydro-Pyrrolo-Pyrazole Heterocycles," Journal of Organic Chemistry, vol. 85, no. 9, pp. 6044 - 6059, American Chemical Society, May 2020.
The definitive version is available at https://doi.org/10.1021/acs.joc.0c00535
Department(s)
Chemistry
International Standard Serial Number (ISSN)
1520-6904; 0022-3263
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2025 American Chemical Society, All rights reserved.
Publication Date
01 May 2020
