Efficient Asymmetric Synthesis of P-Chiral Phosphine Oxides via Properly Designed and Activated Benzoxazaphosphinine-2-oxide Agents
摘要:
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.
General and Stereoselective Method for the Synthesis of Sterically Congested and Structurally Diverse <i>P</i>-Stereogenic Secondary Phosphine Oxides
作者:Zhengxu S. Han、Hao Wu、Yibo Xu、Yongda Zhang、Bo Qu、Zhibin Li、Donald R. Caldwell、Keith R. Fandrick、Li Zhang、Frank Roschangar、Jinhua J. Song、Chris H. Senanayake
DOI:10.1021/acs.orglett.7b00568
日期:2017.4.7
A general and efficient method for the synthesis of bulky and structurally diverse P-stereogenic chiral secondary phosphine oxides (SPOs) by using readily available chiral amino alcohol templates is described. These chiral SPOs could be used as chiral building blocks for the synthesis of difficult-to-access bulky P-stereogenic phosphine compounds or ligands for organic catalysis.