Chiral bicyclic guanidine has been found to catalyze the phospha-Michael reactions of diaryl phosphine oxide to nitroalkenes with high enantioselectivities, offering a direct methodology to prepare chiral beta-aminophosphine oxides and beta-aminophosphines.
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Synthesis of Chiral α-Substituted β-Aminophosphine Derivatives through Asymmetric Hydrophosphinylation Utilizing Secondary Phosphine Sulfides.
Chem Asian J
December 2022
Department of Pharmaceutical Chemistry, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo, 192-0392, Japan.
The organocatalytic enantioselective hydrophosphinylation of various secondary phosphine sulfides with aromatic and aliphatic nitroalkenes is presented in this study. The reaction produced chiral β-nitrophosphine sulfides with excellent yields and enantioselectivities (up to 99% yield and 99% ee). Furthermore, the chiral β-nitrophosphine sulfides can be easily converted into α-substituted β-aminophosphine, which is a family of useful P, N-ligands and phosphine catalysts.
View Article and Find Full Text PDFRh-Catalyzed Asymmetric Hydrogenation of ()-β-Phosphorylated Enamides: Highly Enantioselective Access to β-Aminophosphines.
Org Lett
November 2019
Dalian Institute of Chemical Physics, Chinese Academy of Sciences , 457 Zhongshan Road , Dalian 116023 , China.
A catalytic asymmetric hydrogenation of β-phosphorylated enamides for enantioselective access to optically active β-aminophosphine derivatives is reported. Critical to the success of this method was the employment of rhodium catalysis in concert with an unsymmetrical hybrid chiral phosphine-phosphoramidite ligand. A wide range of aromatic β-phosphorylated enamides could be hydrogenated in full conversion and with perfect enantioselectivity even at low catalyst loadings (S/C = 1000).
View Article and Find Full Text PDFP-Stereogenic β-Aminophosphines: Preparation and Applications in Enantioselective Organocatalysis.
J Org Chem
March 2017
Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada.
The synthesis of stereodefined β-aminophosphines having both carbon- and phosphorus-based chirality centers is described. The method involves resolution of a mixture of β-aminophosphine oxide diastereomers accessed by ring-opening of an amino alcohol-derived cyclic sulfamidate. A stereospecific, borane-promoted reduction of β-aminophosphine oxides, which occurs under mild conditions and with inversion of configuration at phosphorus, is a key step in this process.
View Article and Find Full Text PDFRecent developments in the synthesis and utilization of chiral β-aminophosphine derivatives as catalysts or ligands.
Chem Soc Rev
March 2016
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemsitry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, China. and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032, China.
In the last few years, the research area of chiral β-aminophosphines capable of promoting a wide range of diverse organic transformations has attracted more attention. Their derivatives constitute attractive reagents towards this end, due to their stability, low toxicity and ease of handling. These novel β-aminophosphine derivatives are potentially useful as organocatalysts and ligands in metal-catalysed reactions.
View Article and Find Full Text PDFA versatile synthesis of chiral β-aminophosphines.
Org Biomol Chem
June 2016
Department of Chemistry, University of Toronto, Toronto, ON M5S 3H6, Canada.
A method for the preparation of chiral β-aminophosphines having substituted P-aryl groups is described. Ring-opening of cyclic sulfamidates with metal diarylphosphinites yields β-aminophosphine oxides, which are then reduced to the corresponding phosphines. Effects of the diarylphosphinite countercation on the regioselectivity of the ring-opening reaction (P- versus O-alkylation) are discussed.
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