A versatile synthesis of chiral β-aminophosphines

2016 ◽  
Vol 14 (24) ◽  
pp. 5665-5672 ◽  
Author(s):  
Hsin Y. Su ◽  
Yixiong Song ◽  
Mark S. Taylor
Keyword(s):  
Ring Opening ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Sterically Hindered

A protocol for the synthesis of chiral β-aminophosphines by ring-opening of cyclic sulfamidates with metallated secondary phosphine oxides is described. It allows access to previously unknown derivatives having electron-deficient, electron-rich and sterically hindered P-aryl substituents.

Diastereoselective Synthesis of P-Stereogenic Secondary Phosphine Oxides (SPOs) Bearing a Chiral Substituent by Ring Opening of (+)-Limonene Oxide with Primary Phosphido Nucleophiles

2020 ◽  
Vol 85 (22) ◽  
pp. 14516-14526
Author(s):  
Amber N. Zimmerman ◽  
Rebecca S. Xu ◽  
Samantha C. Reynolds ◽  
Chase A. Shipp ◽  
Derrick J. Marshall ◽  
...  
Keyword(s):  
Ring Opening ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Diastereoselective Synthesis ◽  
Limonene Oxide

Thermal stability of primary and secondary phosphine oxides formed as a reaction of phosphine oxide with ketones

2016 ◽  
Vol 191 (11-12) ◽  
pp. 1480-1481 ◽  
Author(s):  
E. V. Gorbachuk ◽  
E. K. Badeeva ◽  
S. A. Katsyuba ◽  
P. O. Pavlov ◽  
Kh. R. Khayarov ◽  
...  
Keyword(s):  
Thermal Stability ◽  
Phosphine Oxide ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Thermal Stability Of

Preparation of Optically Pure Tertiary Phosphine Oxides via the Addition ofP-Stereogenic Secondary Phosphine Oxide to Activated Alkenes

2016 ◽  
Vol 81 (17) ◽  
pp. 7644-7653 ◽  
Author(s):  
Ji-Ping Wang ◽  
Shao-Zhen Nie ◽  
Zhong-Yang Zhou ◽  
Jing-Jing Ye ◽  
Jing-Hong Wen ◽  
...  
Keyword(s):  
Phosphine Oxide ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Tertiary Phosphine ◽  
Optically Pure

Facile synthesis of chiral 1,2-chlorohydrins via the ring-opening of meso-epoxides catalyzed by chiral phosphine oxides

Tetrahedron ◽  
2013 ◽  
Vol 69 (14) ◽  
pp. 3075-3081 ◽  
Author(s):  
Shunsuke Kotani ◽  
Haruka Furusho ◽  
Masaharu Sugiura ◽  
Makoto Nakajima
Keyword(s):  
Ring Opening ◽  
Phosphine Oxides ◽  
Facile Synthesis

Catalyst- and Solvent-Free Hydrophosphorylation of Ketones with Secondary Phosphine Oxides: Green Synthesis of Tertiary α-Hydroxyphosphine Oxides

Synthesis ◽  
2020 ◽  
Vol 52 (15) ◽  
pp. 2224-2232
Author(s):  
Boris A. Trofimov ◽  
Nina K. Gusarova ◽  
Nina I. Ivanova ◽  
Kseniya O. Khrapova ◽  
Pavel A. Volkov ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Green Chemistry ◽  
Green Synthesis ◽  
Quantum Chemical Calculations ◽  
Quantum Chemical ◽  
Solvent Free ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Intramolecular Hydrogen ◽  
Solvent Free Reaction

Tertiary α-hydroxyphosphine oxides have been synthesized via the catalyst- and solvent-free reaction between available secondary phosphine oxides and aliphatic, aromatic and heteroaromatic ketones at 20–62 °C in near to 96–98% yield. The developed method meets the requirements of green chemistry and the PASE (pot, atom, step economy) paradigm. According to quantum-chemical calculations at the B3LYP/6-311++G(d,p) level, the synthesized hydroxyphosphine oxides feature a weak (≈3 kcal·mol–1) O−H···O=P intramolecular hydrogen bond.

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