870533-22-5Relevant academic research and scientific papers
Electrostatic repulsion and hydrogen-bonding interactions in a simple N-aryl-L-valinamide organocatalyst control the stereoselectivity in asymmetric aldol reactions
Tanimura, Yuya,Yasunaga, Kenji,Ishimaru, Kaori
, p. 6535 - 6539 (2013)
A novel stereocontrol method for asymmetric aldol reactions of aldehydes with ketones is described. The stereoselectivity of the products is controlled by the electrostatic repulsion and hydrogen-bonding interactions of an N-aryl-L-valinamide catalyst. Th
Development of new catalytic enantioselective formation of methylenelactam-based N,O-spirocyclic compounds via ring opening-asymmetric reclosure of hydroxylactams
Sengoku, Tetsuya,Miyoshi, Ayako,Tsuda, Tamaki,Inuzuka, Toshiyasu,Sakamoto, Masami,Takahashi, Masaki,Yoda, Hidemi
, (2020/05/18)
Catalytic enantioselective formation of methylenelactam-based N,O-spirocyclic compounds is developed. Hydroxylactams prepared from N-carbonyl phthalimides and β-amido functionalized allylboronates underwent ring opening-asymmetric reclosure in the presence of catalytic amounts of MgBr2 and a chiral aminophenol to afford the corresponding N,O-spirocyclic compounds in excellent yields and high enantioselectivities.
New chiral zwitterionic phosphorus heterocycles: Synthesis, structure, properties and application as chiral solvating agents
Sheshenev, Andrey E.,Boltukhina, Ekaterina V.,Grishina, Anastasiya A.,Cisa?ova, Ivana,Lyapkalo, Ilya M.,Hii, King Kuok
supporting information, p. 8136 - 8143 (2013/07/27)
A family of new chiral zwitterionic phosphorus-containing heterocycles (zPHC) have been derived from methylene-bridged bis(imidazolines). These structures were unambiguously determined, including single-crystal XRD analysis for two compounds. The stability, acid/base and electronic properties of these dipolar phosphorus heterocycles were subsequently investigated. zPHCs can be successfully employed as a new class of chiral solvating agents for the enantiodifferentiation of chiral carboxylic and sulfonic acids by NMR spectroscopy. The stoichiometry and binding constants for the donor-acceptor complexes formed were established by NMR titration methods. A convenient synthetic approach to a new class of chiral zwitterionic phosphorus-containing heterocycles starting from methylene-bridged bis(imidazolines) was designed and executed. Stability and properties of the synthesized compounds were investigated. The applicability of the designed compounds as chiral solvating agents for the determination of the enantiomeric excesses of chiral acids was demonstrated. Copyright
A highly efficient and practical method for catalytic Asymmetric Vinylogous Mannich (AVM) reactions
Carswell, Emma L.,Snapper, Marc L.,Hoveyda, Amir H.
, p. 7230 - 7233 (2007/10/03)
(Chemical Equation Presented) Very selective but very easy: These are two of the attributes of the asymmetric vinylogous Mannich reactions presented herein. These reactions can be run on a gram scale and in undistilled THF and air (see scheme; TMS = SiMe3). All that is needed is commercially available AgOAc, a readily available amino acid derived phosphine, and a commercially available or easily prepared (one step) siloxyfuran.
