1028374-87-9Relevant academic research and scientific papers
Copper(I)-catalyzed substitution reactions of propargylic amines: Importance of C(sp)-C(sp3) bond cleavage in generation of iminium intermediates
Sugiishi, Tsuyuka,Kimura, Akifumi,Nakamura, Hiroyuki
supporting information; experimental part, p. 5332 - 5333 (2010/07/04)
Substitution reactions of propargylic amines proceed in the presence of copper(I) catalysts. Mechanistic studies showed that C(sp)?C(sp3) bond cleavage assisted by nitrogen lone-pair electrons is essential for the reaction, and the resulting iminium intermediates undergo amine exchange, aldehyde exchange, and alkyne addition reactions. Because iminium intermediates are key to aldehyde?alkyne?amine (A3) coupling reactions, this transformation is effective not only for reconstruction of propargylic amines but also for chiral induction of racemic compounds in the presence of chiral catalysts.
Synthesis of mono- and 1,3-disubstituted allenes from propargylic amines via palladium-catalysed hydride-transfer reaction
Nakamura, Hiroyuki,Ishikura, Makoto,Sugiishi, Tsuyuka,Kamakura, Takaya,Biellmann, Jean-Francois
experimental part, p. 1471 - 1477 (2008/10/09)
Mono- and 1,3-disubstituted allenes were synthesized from the corresponding propargylamines via palladium-catalysed hydride-transfer reaction. In the current transformation, propargylic amines can be handled as allenyl anion equivalents and introduced int
