Journal article

Multistereocenter-Containing Cyclopentanoids from Ynamides via Oxazolidinone-Controlled Nazarov Cyclization

Narasimhulu Manchala, Hanson YL Law, Daniel J Kerr, Rohan Volpe, Romain J Lepage, Jonathan M White, Elizabeth H Krenske, Bernard L Flynn

The Journal of Organic Chemistry | American Chemical Society | Published : 2017

Abstract

Achieving ready-enantioselective access to multistereocenter-containing cyclopentyl rings is an area of great significance to organic synthesis. In this work, we describe a general protocol for accessing multistereocenter-containing cyclopentanoids from simple N-alkynyloxazolidinones (Ox-ynamides). This protocol involves conversion of Ox-ynamides into Ox-activated divinyl and aryl vinyl ketones that undergo facile Nazarov cyclization with excellent chemo-, regio-, and stereocontrol. The Ox auxiliary directs all aspects of reactivity and selectivity, both in the electrocyclization and in the subsequent transformations of the resulting oxyallyl intermediate. Stereoinduction in the electrocycli..

View full abstract

University of Melbourne Researchers

Grants

Awarded by Australian Research Council


Funding Acknowledgements

This research has been supported by the Australian Research Council (DP150103131 and FT120100632). Computer resources were provided by the Australian National Computational Infrastructure National Facility and by the University of Queensland Research Computing Centre.