Enantiodivergent Formation of C–P Bonds: Synthesis of P-Chiral Phosphines and Methylphosphonate Oligonucleotides
作者:Dongmin Xu、Nazaret Rivas-Bascón、Natalia M. Padial、Kyle W. Knouse、Bin Zheng、Julien C. Vantourout、Michael A. Schmidt、Martin D. Eastgate、Phil S. Baran
DOI:10.1021/jacs.9b13898
日期:2020.3.25
Phosphorous Incorporation (PI, abbreviated Π) reagents for the modular, scalable, and stereospecific synthesis of chiral phosphines and methyl-phosphonate nucleotides are reported. Synthesized from trans-limonene oxide, this reagent class displays an unexpected reactivity profile and enables access to chemical space distinct from that of the Phosphorous-Sulfur Incorporation reagents previously disclosed
Efficient Asymmetric Synthesis of <i>P</i>-Chiral Phosphine Oxides via Properly Designed and Activated Benzoxazaphosphinine-2-oxide Agents
作者:Zhengxu S. Han、Navneet Goyal、Melissa A. Herbage、Joshua D. Sieber、Bo Qu、Yibo Xu、Zhibin, Li、Jonathan T. Reeves、Jean-Nicolas Desrosiers、Shengli Ma、Nelu Grinberg、Heewon Lee、Hari P. R. Mangunuru、Yongda Zhang、Dhileep Krishnamurthy、Bruce Z. Lu、Jinhua J. Song、Guijun Wang、Chris H. Senanayake
DOI:10.1021/ja312352p
日期:2013.2.20
A general, efficient, and highly diastereoselective method for the synthesis of structurally and sterically diverse P-chiral phosphine oxides was developed. The method relies on sequential nucleophilic substitution on the versatile chiral phosphinyl transfer agent 1,3,2-benzoxazaphosphinine-2-oxide, which features enhanced and differentiated P N and P-O bond reactivity toward nucleophiles. The reactivities of both bonds are fine-tuned to allow cleavage to occur even with sterically hindered nucleophiles under mild conditions.
PROCESS FOR MAKING NOVEL CHIRAL PHOSPHORUS LIGANDS
申请人:Boehringer Ingelheim International GmbH
公开号:EP2920189B1
公开(公告)日:2017-08-02
US8816112B2
申请人:——
公开号:US8816112B2
公开(公告)日:2014-08-26
[EN] PROCESS FOR MAKING NOVEL CHIRAL PHOSPHORUS LIGANDS<br/>[FR] PROCÉDÉ POUR FABRIQUER DE NOUVEAUX LIGANDS DU PHOSPHORE CHIRAUX
申请人:BOEHRINGER INGELHEIM INT
公开号:WO2014078491A1
公开(公告)日:2014-05-22
Disclosed are methods for making chiral phosphorus ligands including chiral phosphines, chiral phosphine oxides, phosphonamides, and aminophosphines. The chiral phosphorus ligands prepared by the methods of the invention are useful as components of chiral catalysts, e.g., transition metal complexes.