Diastereoselective Rh-catalyzed decarboxylative allylation to form quaternary stereocenters using sulfinimine as the directing group
Literature Information
Publication Date
2019-01-24
DOI
10.1039/C8QO01258J
Impact Factor
5.281
Authors
Tongtong Liu, Yunhao Luo, Shende Jiang, Guang Yang
View Original
Abstract
In this paper, we reported for the first time that the diastereoselective Rh-catalyzed decarboxylative allylation of chiral sulfinimines could be used to form quaternary stereocenters. The key factor in giving rise to the successful development of this method was the application of the commercially available and achiral Wilkinson's Rh catalyst. Explained by a plausible mechanism, the sulfinimine group might be a potent directing group chelated with Rh to construct intramolecular steric hindrance. In addition, broad functional group tolerance was observed, and we subsequently revealed the various transformations verifying the utility of this method for rapidly accessing complex enantio-enriched polycyclic compounds.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
2-Methyl-2-propanyl 4-iodo-1-piperidinecarboxylate
CAS Number:
301673-14-3
Molecular Formula:
C10H18INO2
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