dc.contributor.author |
Kutwal, Mahesh S. |
|
dc.contributor.author |
Appayee, Chandrakumar |
|
dc.date.accessioned |
2017-05-23T10:26:51Z |
|
dc.date.available |
2017-05-23T10:26:51Z |
|
dc.date.issued |
2017-08 |
|
dc.identifier.citation |
Kutwal, Mahesh S. and Appayee, Chandrakumar, “Highly regio- and enantioselective g-alkylation of linear a,b-Unsaturated aldehydes”, European Journal of Organic Chemistry, DOI: 10.1002/ejoc.201700645, May 2017. |
en_US |
dc.identifier.issn |
1434-193X |
|
dc.identifier.issn |
1099-0690 |
|
dc.identifier.uri |
https://repository.iitgn.ac.in/handle/123456789/2945 |
|
dc.identifier.uri |
http://dx.doi.org/10.1002/ejoc.201700645 |
|
dc.description.abstract |
Asymmetric alkylation is one of the most useful carbon-carbon bond forming reactions in synthetic organic chemistry. Chiral amine catalyzed alkylation reactions often lack regioselectivity due to multiple reactive centers. Particularly, alkylation of linear 2-enals through dienamine catalysis produces a mixture of regioisomers due to the reactive a- and b-positions. There are few attempts made to mask a-reactive center to achieve g-selectivity. Controlling enantioselectivity at the remote g-position has also been found to be quite challenging. We have achieved a highly regioselective g-alkylation of linear a,b-unsaturated aldehydes using trifluoroethanol (TFE) as a co-solvent. Further, we have demonstrated an in situ kinetic resolution for the enantioenrichment of g-alkylated products. This methodology brings a novel activation of electrophile facilitated by TFE and an in situ kinetic resolution to achieve excellent selectivity in dienamine catalysis. |
en_US |
dc.description.statementofresponsibility |
by Mahesh S. Kutwal and Chandrakumar Appayee |
|
dc.format.extent |
Vol. 2017, no. 29, pp. 4230–4234 |
|
dc.language.iso |
en_US |
en_US |
dc.publisher |
Wiley |
en_US |
dc.title |
Highly regio- and enantioselective g-alkylation of linear a,b-Unsaturated aldehydes |
en_US |
dc.type |
Article |
en_US |
dc.relation.journal |
European Journal of Organic Chemistry |
|