28256-56-6Relevant academic research and scientific papers
Palladium-catalysed direct cross-coupling of secondary alkyllithium reagents
Vila, Carlos,Giannerini, Massimo,Hornillos, Valentin,Fananas-Mastral, Martin,Feringa, Ben L.
, p. 1361 - 1367 (2014/03/21)
Palladium-catalysed cross-coupling of secondary C(sp3) organometallic reagents has been a long-standing challenge in organic synthesis, due to the problems associated with undesired isomerisation or the formation of reduction products. Based on our recently developed catalytic C-C bond formation with organolithium reagents, herein we present a Pd-catalysed cross-coupling of secondary alkyllithium reagents with aryl and alkenyl bromides. The reaction proceeds at room temperature and on short timescales with high selectivity and yields. This methodology is also applicable to hindered aryl bromides, which are a major challenge in the field of metal catalysed cross-coupling reactions.
Enantioselective protonation of samarium enolates derived from α- heterosubstituted ketones and lactone by SmI2-mediated reduction
Nakamura, Yutaka,Takeuchi, Seiji,Ohgo, Yoshiaki,Yamaoka, Makoto,Yoshida, Akihiro,Mikami, Koichi
, p. 4595 - 4620 (2007/10/03)
SmI2-mediated reductive cleavage of α-heterosubstituents of α-alkyl or α-aryl ketones and lactone gave the corresponding 'thermodynamic samarium enolates'. Enantioselective protonation of the samarium enolates with C2- symmetric chiral diols afforded the corresponding ketones and lactone in moderate to high enantioselectivities.
