214219-69-9Relevant articles and documents
Inverse demand [4+2] cycloaddition reactions of allenamides: Reactivity scopes of an electron deficient variant of allenamines
Wei, Lin-Li,Xiong, Hui,Douglas, Christopher J.,Hsung, Richard P.
, p. 6903 - 6907 (1999)
The synthesis and reactivity of a series of new allenamides are described. These electron deficient variants of allenamines are more stable than allenamines but possess comparable reactivity. Particularly, oxazolidinone and imidazolidinone substituted allenamides undergo efficient inverse demand [4+2] cycloaddition reactions with heterodienes, leading to unique pyranyl heterocycles. The reactivity differences between various allenamides containing different substitution patterns around the nitrogen atom are illustrated.
Nickel-catalyzed synthesis of stereochemically defined enamides via Bi- and tricomponent coupling reaction
Liu,De Nisi,Cerveri,Monari,Bandini
, p. 5034 - 5037 (2017/11/06)
The stereoselective synthesis of (E)-trisubstituted tertiary enamides is documented via site-selective Ni-catalyzed β-arylation of allenamides with boronic acids in high yields (up to 89%). The nucleophilic character of the "organo-Ni" intermediates is further exploited to implement a one-pot tricomponent procedure involving the final allylation of aldehydes (yields up to 93%). Mechanistic insights and efficiency on a gram scale process were also documented.
On the base-induced isomerization of cyclic propargylamides to cyclic allenamides
Fenández, Israel,Monterde, María I.,Plumet, Joaquín
, p. 6029 - 6031 (2007/10/03)
The reaction of lactams 4 (n = 1-5) with propargyl bromide affords propargylamides or allenylamides depending on the ring-size. Theoretical calculations support the dependence of the extension of the isomerization on the ring-size.
