Highly regio- and enantioselective g-alkylation of linear a,b-Unsaturated aldehydes

Show simple item record

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

Files in this item

Files Size Format View

There are no files associated with this item.

This item appears in the following Collection(s)

Show simple item record

Search Digital Repository


My Account