A Cascade Reaction of Cinnamyl Azides with Acrylates Directly Generates Tetrahydro-Pyrrolo-Pyrazole Heterocycles

Angela S. Carlson, En Chih Liu, Joseph J. Topczewski

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
Pages (from-to)6044-6059
Number of pages16
JournalJournal of Organic Chemistry
Volume85
Issue number9
DOIs
StatePublished - May 1 2020

PubMed: MeSH publication types

  • Journal Article

Fingerprint Dive into the research topics of 'A Cascade Reaction of Cinnamyl Azides with Acrylates Directly Generates Tetrahydro-Pyrrolo-Pyrazole Heterocycles'. Together they form a unique fingerprint.

Cite this