Synthesis of dienamides via the reaction of nitrile with allylindium reagents and intramolecular acyl group quenching cascade

Bulletin of the Korean Chemical Society

Volumn 31, Issue 8, 2010, Pages 2351-2356

  Kim, Sung Hwan ^a   Kim, Yu Mi ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

Allylation; Barbier reaction; Dienamides; Indium; Nitrile

Indexed keywords

ACYL GROUP; ALLYLATIONS; AMIDE MOIETIES; BARBIER REACTION; DIENAMIDES; IMINE INTERMEDIATE; NITRILE;

ADDITION REACTIONS; AMIDES; INDIUM; QUENCHING; SYNTHESIS (CHEMICAL);

CYANIDES;

EID: 77956109847     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2010.31.8.2351     Document Type: Article

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35. Actually, the proton He appeared as a doublet due to a small meta-coupling (J = 2.4 Hz) at 7.11 ppm, while the proton He' also appeared as a doublet (J = 2.7 Hz) at 7.18 ppm.
36. When we used N-allyl-N-benzoyl derivative as a substrate instead of N-tosyl-N-benzoyl derivative 1a, we could not obtain the products, presumably because the N-allylphenyl group is not a good leaving group as compared to the N-tosylphenyl moiety in the case of 1a. The reaction showed sluggish reactivity and much of the starting materials were decomposed to many intractable polar compounds.