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

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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


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