We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Stereoselective Synthesis of Polysubstituted Conjugated Dienes Enabled by Photo‐Driven Sequential Sigmatropic Rearrangement.
- Authors
Ji, Xin; Shen, Chaoren; Ni, Yuhao; Si, Zhi‐Yao; Wang, Yuzhu; Zhi, Xinrong; Zhao, Yuting; Peng, Huiling; Liu, Lu
- Abstract
We here reported a highly stereoselective method for the synthesis of polysubstituted conjugated dienes from α‐aryl α‐diazo alkynyl ketones and pyrazole‐substituted unsymmetric aminals under mild conditions, which was promoted by photo‐irridation and involved with 1,6‐dipolar intermediate and quadruple sigmatropic rearrangements, was successfully developed. In this transformation, the cleavage of four bonds and the recombination of five bonds were implemented in one operational step. This protocol provided a modular tool for constructing dienes from amines, pyrazoles and α‐alkynyl‐α‐diazoketones in one‐pot manner. The results of mechanistic investigation indicated that the plausible reaction path underwent the 1,6‐sigmatropic rearrangement instead of the 1,5‐sigmatropic rearrangement.
- Subjects
CLAISEN rearrangement; SIGMATROPIC rearrangements; DIOLEFINS; SCISSION (Chemistry); WOLFF rearrangement; PYRAZOLES; DIAZO compounds; KETONES
- Publication
Angewandte Chemie, 2024, Vol 136, Issue 24, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202400805