1989
DOI: 10.1016/s0040-4020(01)80145-9
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Functionalized chloroenamines in aminocyclopropane synthesis I. — bicyclic and pentacyclic lactams from carbamoylated chloroenamines

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Cited by 11 publications
(4 citation statements)
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“…The feasibility of this approach was demonstrated in a model reaction. The conversion of 7a with phenyl isocyanate 23 yielded 69% of the desired product 15 (Scheme 4). Interestingly, the conversion of 7a,b with alkyl isocyanates such as hexyl and cyclohexyl isocyanate failed, and the enamines 7a,b were recovered.…”
Section: Scheme 2 General Synthetic Scheme Toward Enaminesmentioning
confidence: 99%
“…The feasibility of this approach was demonstrated in a model reaction. The conversion of 7a with phenyl isocyanate 23 yielded 69% of the desired product 15 (Scheme 4). Interestingly, the conversion of 7a,b with alkyl isocyanates such as hexyl and cyclohexyl isocyanate failed, and the enamines 7a,b were recovered.…”
Section: Scheme 2 General Synthetic Scheme Toward Enaminesmentioning
confidence: 99%
“…The cyclic chloroenamines 127 can elegantly be converted to β-ACC derivatives 128 by a domino 1,4addition-cyclization sequence (Scheme 36). Addition of cyanide 53 or succinimide 54 proceeded with high stereoselectivity, placing the nucleophile on the exo side of the bicyclic framework. Quite instructively, the amino function in 128 is not protected by an acceptor group; nevertheless, the geminally located electron-withdrawing group obviously is sufficient to render the molecules stable.…”
Section: β-Accs From β-Dehydroamino Acidsmentioning
confidence: 99%
“…It should be noted that a similar C−N bond cleavage of an orthoamide was reported in a previous study. 15 The second C−N bond cleavage is facilitated by the deprotonation of IM6 to generate the anion IM7, which dissociates into the 1,2-diimine 7 to form the cyclic dienolate IM8 with an activation barrier of 28.1 kcal/mol. Finally, the protonation of IM8 forms γ-lactam 2m (proton pathway).…”
mentioning
confidence: 99%
“…IM4 then isomerizes to form enamine IM5 , followed by a 1,3-proton shift to afford the more stable intermediate IM6 . It should be noted that a similar C–N bond cleavage of an orthoamide was reported in a previous study . The second C–N bond cleavage is facilitated by the deprotonation of IM6 to generate the anion IM7 , which dissociates into the 1,2-diimine 7 to form the cyclic dienolate IM8 with an activation barrier of 28.1 kcal/mol.…”
mentioning
confidence: 99%