This work was supported by the Ministerio de Educación y Ciencia (MEC, Grant No. CTQ2005-02095/BQU). M.R. thanks the MEC for a Ramón y Cajal contract and M.C.R. thanks the MEC for a Juan de la Cierva contract. We are grateful to the referees for helpful comments.
Control of the Regio- and Stereoselectivity in Diels–Alder Reactions with Quinone Boronic Acids†
Article first published online: 8 DEC 2008
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 48, Issue 2, pages 370–374, January 2, 2009
How to Cite
Redondo, María C., Veguillas, M., Ribagorda, M. and Carreño, M. Carmen. (2009), Control of the Regio- and Stereoselectivity in Diels–Alder Reactions with Quinone Boronic Acids. Angew. Chem. Int. Ed., 48: 370–374. doi: 10.1002/anie.200803428
- Issue published online: 22 DEC 2008
- Article first published online: 8 DEC 2008
- Manuscript Received: 15 JUL 2008
- MEC. Grant Number: CTQ2005-02095/BQU
- Diels–Alder reactions;
- trans-fused adducts
It all adds up: The dienophilic reactivity of 2-methyl-substituted quinones has been substantially increased by the introduction of a boronic acid substituent, which makes them equivalent to a highly reactive quinone. The Diels–Alder reactions of these quinones are followed by spontaneous and stereoselective protodeboronation to give the trans-fused adducts. The boron group is a temporal regiocontroller and leads to the uncommon meta adduct.