Formal Asymmetric Cycloaddition of Activated α,β-Unsaturated Ketones with α‑Diazomethylphosphonate Mediated by a Chiral Silver SPINOL Phosphate Catalyst

Published on 2019-01-11T19:19:47Z (GMT) by
An efficient method for preparing highly functionalized chiral nonspiro-phosphonyl­pyrazolines via an asymmetric formal 1,3-dipolar cycloaddition reaction of α-diazomethyl­phosphonate with activated, acyclic α,β-unsaturated ketones, bearing an additional nitrile electron-withdrawing group, has been developed, utilizing an in situ generated chiral silver phosphate catalyst, affording excellent stereoselectivities (up to 98% <i>ee</i>, 99:1 <i>dr</i>) and yields (up to 95%). A stepwise mechanism is proposed based upon density functional M11 calculations.

Cite this collection

Zheng, Bo; Chen, Haohua; Zhu, Lei; Hou, Xiqiang; Wang, Yan; Lan, Yu; et al. (2019): Formal Asymmetric Cycloaddition of Activated α,β-Unsaturated

Ketones with α‑Diazomethylphosphonate Mediated by a Chiral

Silver SPINOL Phosphate Catalyst. ACS Publications. Collection.