7252-19-9Relevant articles and documents
Synthesis of 3-Aryl-1-aminopropane Derivatives: Lithiation-Borylation-Ring-Opening of Azetidinium Ions
Casoni, Giorgia,Myers, Eddie L.,Aggarwal, Varinder K.
, p. 3241 - 3253 (2016/09/12)
In situ generated 2-phenyl-azetidinium ylides react with boronic esters to form acyclic γ-dimethylamino tertiary boronic esters. The transformation is believed to involve the formation of a zwitterionic boronate, which subsequently undergoes ring-opening 1,2-migration, which is promoted by the relief of ring strain. Owing to the configurational instability of the initially formed ylides, which appear to be in equilibrium with the open-chain carbene form, the reaction is not stereospecific. The C-B bond of the γ-dimethylamino tertiary boronic esters can be transformed into a variety of functional groups (C-OH, C-vinyl, C-H, C-BF3), thus giving a diverse selection of 3-aryl-1-aminopropanes, which represent a privileged motif among drug molecules.
Conjugated-triene intermediates in the Sommelet-Hauser rearrangement of cyclic 1-methyl-2-phenylammonium 1-methylides
Sumiya,Shirai,Sato
, p. 36 - 40 (2007/10/02)
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