English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT

Released

Journal Article

Scalable and Highly Diastereo- and Enantioselective Catalytic Diels−Alder Reaction of α,β - Unsaturated Methyl Esters

MPS-Authors
/persons/resource/persons191809

Gatzenmeier,  Tim
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons226584

Turberg,  Mathias
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons216846

Yepes,  Diana
Research Group Bistoni, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons191820

Xie,  Youwei
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons216825

Neese,  Frank
Research Department Neese, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons216804

Bistoni,  Giovanni
Research Group Bistoni, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58764

List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

External Resource
No external resources are shared
Supplementary Material (public)
There is no public supplementary material available
Citation

Gatzenmeier, T., Turberg, M., Yepes, D., Xie, Y., Neese, F., Bistoni, G., et al. (2018). Scalable and Highly Diastereo- and Enantioselective Catalytic Diels−Alder Reaction of α,β - Unsaturated Methyl Esters. Journal of the American Chemical Society, 140(40), 12671-12676. doi:10.1021/jacs.8b07092.


Cite as: http://hdl.handle.net/21.11116/0000-0002-57A0-7
Abstract
Despite tremendous advances in enantioselective catalysis of the Diels−Alder reaction, the use of simple α,β-unsaturated esters, one of the most abundant and useful class of dienophiles, is still severely limited in scope due to their low reactivity. We report here a catalytic asymmetric Diels−Alder methodology for a large variety of α,β-unsaturated methyl esters and different dienes based on extremely reactive silylium imidodiphos-phorimidate (IDPi) Lewis acids. Mechanistic insights from accurate domain-based local pair natural orbital coupled-cluster (DLPNO-CCSD(T)) calculations rationalize the catalyst control and stereochemical outcome.