Synthesis of γ-hydroxypropyl P-chirogenic (±)-phosphorus oxide derivatives by regioselective ring-opening of oxaphospholane 2-oxide precursors

Beilstein Journal of Organic Chemistry

Nissan Ashkenazi¹  Iris Binyamin¹  Shoval Meidan-Shani¹ 

[1] Department of Organic Chemistry, IIBR-Israel Institute for Biological Research, P.O. Box 19, Ness Ziona, 74100, Israel;

关键词: chirogenic phosphorus;    Grignard reagents;    oxaphospholanes;    phosphinates;    phosphine oxides;   

DOI  :  10.3762/bjoc.11.143

来源: DOAJ

【 摘 要 】

The synthesis of P-chirogenic (±)-phosphine oxides and phosphinates via selective nucleophilic ring opening of the corresponding oxaphospholanes is described. Two representative substrates: the phosphonate 2-ethoxy-1,2-oxaphospholane 2-oxide and the phosphinate 2-phenyl-1,2-oxaphospholane 2-oxide were reacted with various Grignard reagents to produce a single alkyl/aryl product. These products may possess further functionalities in addition to the phosphorus center such as the γ-hydroxypropyl group which results from the ring opening and π-donor moieties such as aryl, allyl, propargyl and allene which originates from the Grignard reagent.

【 授权许可】

Unknown