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

Catalytic Asymmetric Synthesis of P-Stereogenic Phosphines: Beyond Precious Metals

Synlett ◽  
2020 ◽  
Author(s):  
David S. Glueck
Keyword(s):  
Asymmetric Synthesis ◽  
Asymmetric Catalysis ◽  
Palladium Catalysts ◽  
Precious Metals ◽  
Synthetic Methods ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Chiral Epoxides ◽  
Earth Abundant ◽  
Limonene Oxide

AbstractMetal-catalyzed asymmetric synthesis of P-stereogenic phosphines is a potentially useful approach to a class of chiral ligands with valuable applications in asymmetric catalysis. We introduced this idea with chiral platinum and palladium catalysts, exploiting rapid pyramidal inversion in diastereomeric metal–phosphido complexes (ML*(PRR′)) to control phosphorus stereochemistry. This Account summarizes our attempts to develop related synthetic methods using earth-abundant metals, especially copper, in which weaker metal–ligand bonds and faster substitution processes were expected to result in more active catalysts. Indeed, precious metals were not required. Without any transition metals at all, we exploited related P-epimerization processes to prepare enantiomerically pure phosphiranes and secondary phosphine oxides (SPOs) from commercially available chiral epoxides.1 Introduction2 Copper-Catalyzed Phosphine Alkylation3 Copper-Catalyzed Tandem Phosphine Alkylation/Arylation4 Nickel-Catalyzed Phosphine Alkylation5 Proton-Mediated P-Epimerization in Synthesis of Chiral Phosphiranes6 Diastereoselective Synthesis of P-Stereogenic Secondary Phosphine Oxides (SPOs) from (+)-Limonene Oxide7 Conclusions

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.

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
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