ja312352p_si_008.pdf (1.77 MB)
Download fileEfficient Asymmetric Synthesis of P‑Chiral Phosphine Oxides via Properly Designed and Activated Benzoxazaphosphinine-2-oxide Agents
journal contribution
posted on 2016-02-19, 22:05 authored by 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. SenanayakeA 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.