Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 19, Issue 25, Pages 5595-5606Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob00670c
Keywords
-
Categories
Funding
- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo - FAPESP [2019/25634-9, 2016/21676-0, 2014/15962-5, 2015/08539-1, 2016/17328-7, 2019/16026-5, 2017/18485-1]
- Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior - CAPES [001, 23038.006960/2014-65]
- NSERC Discovery program
Ask authors/readers for more resources
This study reports the regio- and diastereoselective synthesis of oxazolidinones via a Pd-catalyzed vicinal C-N/C-Cl bond-forming reaction from internal alkenes of allylic carbamates. The products are obtained in high yields and excellent diastereoselectivities. Detailed mechanistic studies were carried out to describe the reaction process, including the role of Cu(ii) in a C-Cl bond-forming mechanism step.
The regio- and diastereoselective synthesis of oxazolidinones via a Pd-catalyzed vicinal C-N/C-Cl bond-forming reaction from internal alkenes of allylic carbamates is reported. The oxazolidinones are obtained in yields of 44 to 95% with high to excellent diastereoselectivities (from 6 : 1 to >20 : 1 dr) from readily available precursors. This process is scalable, and the products are suitable for the synthesis of useful amino alcohols. A detailed theoretical and experimental mechanistic study was carried out to describe that the reaction proceeds through an anti-aminopalladation of the alkene followed by an oxidative C-Pd(ii) cleavage with retention of the carbon stereochemistry to yield the major diastereomer. The role of Cu(ii) in a C-Cl bond-forming mechanism step has also been proposed.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available