dc.contributor.author |
Hepburn, Hamish B. |
dc.contributor.author |
Magagnano, Giandomenico |
dc.contributor.author |
Melchiorre, Paolo |
dc.date.accessioned |
2018-01-15T16:04:16Z |
dc.date.accessioned |
2018-02-15T10:27:32Z |
dc.date.available |
2018-01-15T16:04:16Z |
dc.date.available |
2018-02-15T10:27:32Z |
dc.date.issued |
2016 |
dc.identifier.uri |
http://hdl.handle.net/2072/226320 |
dc.identifier.uri |
http://hdl.handle.net/2072/305755 |
dc.language.iso |
eng |
dc.publisher |
Thieme E-Journals - Synthesis |
dc.relation |
Mineco |
dc.relation |
Agaur |
dc.relation |
ERC |
dc.relation |
Marie Curie |
dc.relation |
SEVERO OCHOA EXCELLENCE ACCREDITATION |
dc.relation.ispartof |
Chemistry Journal |
dc.rights |
© Georg Thieme Verlag Stuttgart · New York |
dc.subject.other |
enantioselective catalysis |
dc.subject.other |
organocatalysis |
dc.subject.other |
Mannich-type reaction |
dc.subject.other |
photochemistry |
dc.subject.other |
synthetic methods |
dc.title |
Light-triggered Enantioselective Organocatalytic Mannich-type Reaction |
dc.type |
info:eu-repo/semantics/article |
dc.relation.projectID |
CTQ2013-45938-P |
dc.relation.projectID |
SEV-2013-0319 |
dc.relation.projectID |
2014 SGR 1059 |
dc.relation.projectID |
info:eu-repo/grantAgreement/EC/FP7/ 278541 |
dc.identifier.doi |
https://dx.doi.org/10.1055/s-0036-1588606 |
dc.rights.accessLevel |
info:eu-repo/semantics/openAccess |
dc.description.abstract |
Abstract Disclosed herein is a photochemical organocatalytic strategy for the direct enantioselective Mannich-type reaction of 2-alkyl-benzophenones and cyclic imines. The chemistry exploits the light-triggered enolization of 2-alkyl-benzophenones to generate transient hydroxy-o-quinodinomethanes. These fleeting intermediates can be stereoselectively intercepted by imines upon activation with a chiral organic catalyst, derived from natural cinchona alkaloids. The developed method uses mild conditions, simple sources of illumination and easily available substrates and catalysts, affording enantioenriched chiral amines that are difficult to synthesize by other approaches. |