84530-49-4Relevant academic research and scientific papers
β- and γ-disubstituted olefins: Substrates for copper-catalyzed asymmetric allylic substitution
Falciola, Caroline A.,Tissot-Croset, Karine,Reyneri, Hugo,Alexakis, Alexandre
supporting information; scheme or table, p. 1090 - 1100 (2009/05/30)
The copper-catalyzed asymmetric allylic alkylation has shown through many examples that it is a powerful means to generate stereogenic centers with mono β- and γ-substituted olefinic substrates. However, little has been reported about more substituted olefinic patterns, such as β-disubstituted allylic electrophiles. In this paper, we show that a simple procedure using easily accessible Grignard reagents and as low as 3 mol% of copper/ligand can promote high to nearly perfect enantioselectivities (up to >99% ee) with very good γ-selectivities on a wide panel of aliphatic or aromatic β-disubstituted substrates.
AZO ANIONS IN SYNTHESIS. USE OF TRITYL- AND DIPHENYL-4-PYRIDYLMETHYLHYDRAZONES FOR REDUCTIVE C-C BOND FORMATION.
Baldwin, Jack E.,Adlington, Robert M.,Bottaro, Jeffrey C.,Kolhe, Jayant N.,Newington, Ian M.,Perry, Matthew W. D.
, p. 4235 - 4246 (2007/10/02)
The lithium salts of trityl- and diphenyl-4-pyridylmethyl-hydrazones of both aldehydes and ketones react with electrophiles (alkyl halides, aldehydes, ketones, crotonates) at low temperature to form C-trapped azo compounds; these intermediates decompose homolytically with loss of nitrogen below room temperature and can be diverted in a synthetically useful way to alkanes, alkenes, alcohols or saturated esters.
Azo Anions in Synthesis. Use of Trityl- and Diphenyl-4-pyridylmethyl-hydrazones for Reductive C-C Bond Formation from Aldehydes and Ketones
Baldwin, Jack E.,Bottaro, Jeffrey C.,Kolhe, Jayant N.,Adlington, Robert M.
, p. 22 - 23 (2007/10/02)
The lithium salts for trityl- and diphenyl-4-pyridylmethyl-hydrazones of both aldehydes and ketones react with electrophiles (alkyl halides, aldehydes, and ketones) at low temperature to form C-trapped azo compounds; these intermediates decompose homolytically with loss of nitrogen below room temperature and can be diverted in a synthetically useful way to alkanes, or alkenes, or alcohols.
