Chiral iminoesters derived from D-glyceraldehyde in [3 + 2] cycloaddition reactions. Asymmetric synthesis of a key intermediate in the synthesis of neuramidinase inhibitors.

Abstract

Silver-catalyzed endo-selective and copper-catalyzed exo-selective asymmetric [3 + 2] cycloadditions of acrylates to chiral iminoesters derived from D-glyceraldehyde have been investigated. The reaction diastereoselectively provides highly functionalized pyrrolidines. This approach was used to develop the first asymmetric synthesis of a key intermediate in the synthesis of pyrrolidine influenza neuramidinase inhibitors.

• Authors: José A Gálvez, María D Díaz-de-Villegas, Miriam Alías, Ramón Badorrey
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 78 Issue 22 Pg. 11404-13 (Nov 15 2013) ISSN: 1520-6904 [Electronic] United States
• PMID: 24143968 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Enzyme Inhibitors
• Esters
• Imines
• Pyrrolidines
• Glyceraldehyde
• Neuraminidase

Topics

• Cyclization
• Dose-Response Relationship, Drug
• Enzyme Inhibitors (chemical synthesis, chemistry, pharmacology)
• Esters (chemical synthesis, chemistry, pharmacology)
• Glyceraldehyde (chemistry)
• Imines (chemical synthesis, chemistry, pharmacology)
• Molecular Structure
• Neuraminidase (antagonists & inhibitors, metabolism)
• Orthomyxoviridae (enzymology)
• Pyrrolidines (chemical synthesis, chemistry, pharmacology)
• Structure-Activity Relationship