Direct organocatalytic in situ generation of novel push–pull dienamines: application in tandem Claisen–Schmidt/iso-aromatization reactions

Ramachary, Dhevalapally B. ; Ramakumar, K. ; Kishor, M. (2005) Direct organocatalytic in situ generation of novel push–pull dienamines: application in tandem Claisen–Schmidt/iso-aromatization reactions Tetrahedron Letters, 46 (41). pp. 7037-7042. ISSN 0040-4039

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Official URL: http://doi.org/10.1016/j.tetlet.2005.08.051

Related URL: http://dx.doi.org/10.1016/j.tetlet.2005.08.051

Abstract

A new, green, regioselective, one-step, tandem reaction of an aldehyde possessing a non-enolizable carbonyl function with a highly substituted cyclohex-2-enone, under amine catalysis afforded highly substituted phenols or 2-arylidenecyclohexanones, respectively. The yields and regioselectivities were good. Evidence for a pathway involving formation of novel push–pull dienamines is presented along with examples demonstrating the amenability of the process to combinatorial chemistry.

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