62056-35-3Relevant academic research and scientific papers
Direct Reduction of Allylic Alcohols Using Isopropanol as Reductant
Sai, Masahiro
supporting information, p. 3482 - 3487 (2018/09/14)
The lithium cation-catalyzed direct reduction of allylic alcohols to alkenes using isopropanol as a hydride donor was developed. The hydride transfer of the in situ-generated lithium isopropoxide to an allylic cation is the key process in this transformation. The reaction generates only water and acetone as byproducts, which highlights the synthetic utility of this method. (Figure presented.).
Palladium-catalyzed allylic arylation of allylic ethers with arylboronic acids using hydrazone ligands
Mino, Takashi,Kogure, Taketo,Abe, Taichi,Koizumi, Tomoko,Fujita, Tsutomu,Sakamoto, Masami
, p. 1501 - 1505 (2013/05/09)
Unsymmetrical 1,3-diarylpropenes were synthesized in good to high yields by the palladium-catalyzed allylic arylation of allylic ethers, such as a cinnamyl phenyl ether, with a variety of arylboronic acids using a hydrazone 1a-Pd(OAc)2 system in DMAc/H2O. Using this catalyst, eugenol was also synthesized from allyl phenyl ether with (4-hydroxy-3- methoxyphenyl)boronic acid pinacol ester. A palladium-catalyzed allylic arylation of cinnamyl phenyl ether derivatives with a variety of arylboronic acids using 5 mol-% of a hydrazone 1a-Pd(OAc)2 system in DMAc/H 2O at 50 °C gave 1,3-diarylpropenes in good yields. We also succeeded with the synthesis of eugenol by a palladium-catalyzed allylic arylation. Copyright
Copper-free asymmetric allylic alkylation with grignard reagents
Jackowski, Olivier,Alexakis, Alexandre
supporting information; experimental part, p. 3346 - 3350 (2010/07/15)
(Chemical Equation Presented) Open wide and say AAA: The copper-free asymmetric allylic alkylation reaction of Crignard reagents, catalyzed by N-heter-ocyclic carbenes, is reported for allyl bromide derivatives. This reaction offers good enantioselectivit
Efficient chiral N-heterocyclic carbene/copper(I)-catalyzed asymmetric allylic arylation with aryl Grignard reagents
Selim, Khalid B.,Matsumoto, Yasumasa,Yamada, Ken-Ichi,Tomioka, Kiyoshi
supporting information; experimental part, p. 8733 - 8735 (2010/02/28)
Gamma rules: The title reaction was achieved in a highly regioselective manner using aryl Grignard reagents with monodentate chiral N-heterocyclic carbenel copper(I) catalyst to givediarylvinylmethanes with excellent enantiomeric excess in excellent yield
FeCl3 · 6H2O catalyzed disproportionation of allylic alcohols and selective allylic reduction of allylic alcohols and their derivatives with benzyl alcohol
Wang, Jialiang,Huang, Wen,Zhang, Zhengxing,Xiang, Xu,Liu, Ruiting,Zhou, Xigeng
supporting information; experimental part, p. 3299 - 3304 (2009/09/08)
Iron chloride has been found to be an efficient catalyst for the disproportionation of allylic alcohols, which provides a convenient method for selective transformation of allylic alcohols to alkenes and α,β- unsaturated ketones. Furthermore, this catalytic system is also effective for highly selective allylic reduction of allylic alcohols, allylic ethers, and allylic acetates with benzyl alcohol under neutral and convenient reaction conditions.
Enantioselective iridium-catalyzed allylic arylation
Polet, Damien,Rathgeb, Xavier,Falciola, Caroline A.,Langlois, Jean-Baptiste,El Hajjaji, Samir,Alexakis, Alexandre
supporting information; experimental part, p. 1205 - 1216 (2009/09/06)
We describe herein the development of the first iridium-catalyzed allylic substitution using arylzinc nucleophiles. High enantioselectivities were obtained from the reactions, which used commercially available Grignard reagents as the starting materials. This methodology was also shown to be compatible with halogen/metal exchange reactions. Its synthetic potential is demonstrated by its application towards the formal synthesis of (+)-sertraline.
Copper-catalyzed asymmetric allylic substitution with aryl and ethyl Grignard reagents
Selim, Khalid B.,Yamada, Ken-Ichi,Tomioka, Kiyoshi
supporting information; experimental part, p. 5140 - 5142 (2009/03/11)
Phenyl- and ethyl-magnesium bromides undergo regioselective asymmetric allylic substitution with high enantioselectivity under the catalysis of chiral amidophosphane-copper(i) complexes. The Royal Society of Chemistry.
