Intermolecular Morita-Baylis-Hillman vs. an intramolecular Rauhut-Currier reaction
Rakesh Kumar Verma1, Mansingh Bairwa1, Juli Saini1
1Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi-221005, India. kishorbharadwaj@bhu.ac.in.
Abstract:
Utilising the sensitivity of Morita-Baylis-Hillman (MBH) reactions, a method for chemoselective trapping of enolates for intermolecular MBH (1,2) addition over intramolecular Rauhut-Currier (RC) (1,4) addition has been developed. The sluggish acrylamide served as a source of the initial enolate. While acrylate and acrylonitrile tethered acrylamide showed complete selectivity for the intermolecular MBH reaction, the corresponding enone showed some reactivity for the intramolecular RC reaction. The concept of this reversal offers various opportunities to explore within and outside the domain of MBH and RC reactions. Eventually, the intramolecular RC reaction was also achieved using N-alkylated precursors.
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