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Can enamines be formed from α,β-unsaturated ketones?
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Lucas Brown
Can enamines be formed from α,β-unsaturated ketones?
Stork and Birnbaum have reported (Tetrahedron Lett.1961,10, 313) the formation of dienamine 2 from octalone 1. Alkylation with methyl iodide leads to α-alkylation of the dienamine. Buffer conditions are required for hydrolysis of the dienamine to octalone 4.
Stork and Birnbaum have reported (Tetrahedron Lett.1961,10, 313) the formation of dienamine 2 from octalone 1. Alkylation with methyl iodide leads to α-alkylation of the dienamine. Buffer conditions are required for hydrolysis of the dienamine to octalone 4.
Ok, i made the reaction more general. Also referenced your reply here since although the reaction doenst seem to be reported with pyrrolidine, in general it is possible to add alkyl groups in α,β-unsaturated carbonyl compounds by using secondary amines. Lastly, compounds like 1 above, namely 2 amido dienes can be formed but their synthesis seems more involved according to this: Beilstein J. Org. Chem. 2011, 7, 410–420. doi:10.3762/bjoc.7.53. Not sure why though, which is the actual question!More
. The reaction continues to give the dienamine of the aldol condensation product (Cf., 2 above). Perhaps using acrylonitrile rather than MVK would eliminate the issue of the aldol step. After addition, the less substituted enamine is formed.More
Stork and Birnbaum have reported (Tetrahedron Lett. 1961, 10, 313) the formation of dienamine 2 from octalone 1. Alkylation with methyl iodide leads to α-alkylation of the dienamine. Buffer conditions are required for hydrolysis of the dienamine to octalone 4.
Stork and Birnbaum have reported (Tetrahedron Lett. 1961, 10, 313) the formation of dienamine 2 from octalone 1. Alkylation with methyl iodide leads to α-alkylation of the dienamine. Buffer conditions are required for hydrolysis of the dienamine to octalone 4.
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