Generation, structure and reactivity of tertiary organolithium reagents. Issue 4 (5th December 2014)

• Record Type: Journal Article
• Authors: Perry, Matthew A.; Rychnovsky, Scott D.
• Is Part Of: Natural product reports. Volume 32:Issue 4(2015:Apr.)
• Page Start: 517
• Page End: 533
• Publication Date: 2014-12-05
• Subjects: Natural products -- Periodicals; Produits naturels -- Périodiques; 547.7
• DOI: 10.1039/c4np00125g
• Languages: English
• ISSNs: 0265-0568

Abstract

Abstract : Tertiary organolithium reagents have great potential in natural product synthesis. Recent progress in organolithium generation has made them accessible. Their utility and stereoselectivity in synthesis is discussed. Abstract : Covering: up to 2014 Tertiary alkyllithium reagents are very useful intermediates in synthesis. Alkyllithium reagents with adjacent heteroatoms may be formed stereoselectively or may react stereoselectively, and have been used in the synthesis of alkaloids, C-glycosides and spirocycles. An overview of the generation, reactivity and stereochemistry of tertiary alkyllithium reagents will be presented, as well as examples of their use in organic synthesis. The discussion will be focused on a conceptual understanding of the generation and reactivity of these intermediates. The reactions described herein generate fully substituted carbon atoms, and the forces driving stereoselectivity will be discussed in detail. Where appropriate, computational results will be introduced to provide a better understanding for the structure and reactivity of tertiary alkyllithium reagents.