126377-69-3Relevant academic research and scientific papers
Cooperative titanocene and phosphine catalysis: Accelerated C-X activation for the generation of reactive organometallics
Fleury, Lauren M.,Kosal, Andrew D.,Masters, James T.,Ashfeld, Brandon L.
, p. 253 - 269 (2013/03/14)
The study presented herein describes a reductive transmetalation approach toward the generation of Grignard and organozinc reagents mediated by a titanocene catalyst. This method enables the metalation of functionalized substrates without loss of functional group compatibility. Allyl zinc reagents and allyl, vinyl, and alkyl Grignard reagents were generated in situ and used in the addition to carbonyl substrates to provide the corresponding carbinols in yields up to 99%. It was discovered that phosphine ligands effectively accelerate the reductive transmetalation event to enable the metalation of C-X bonds at temperatures as low as -40 °C. Performing the reactions in the presence of chiral diamines and amino alcohols led to the enantioselective allylation of aldehydes.
Generation of allyl Grignard reagents via titanocene-catalyzed activation of allyl halides
Fleury, Lauren M.,Ashfeld, Brandon L.
supporting information; experimental part, p. 2427 - 2430 (2010/07/04)
A protocol for the generation of allyl Grignard reagents via the catalytic activation of allyl halides is described herein. Subsequent nucleophilic addition to carbonyl derivatives provided the desired homo allylic alcohols in excellent yields (84-99%). E
New methodology for conjugate additions of allylic ligands to α,β-unsaturated ketones: Synthetic and spectroscopic studies
Lipshutz, Bruce H.,Ellsworth, Edmund L.,Dimock, Stuart H.,Smith, Robin A.J.
, p. 4404 - 4410 (2007/10/02)
Michael additions of allylic ligands, including allyl, methallyl, crotyl, and prenyl systems, to a variety of α,β-unsaturated ketones can be effected in synthetically useful yields with allylcopper reagents in the presence of trimethylchlorosilane. Low-te
