%0 Journal Article %A Zheng, Bo %A Chen, Haohua %A Zhu, Lei %A Hou, Xiqiang %A Wang, Yan %A Lan, Yu %A Peng, Yungui %D 2019 %T Formal Asymmetric Cycloaddition of Activated α,β-Unsaturated Ketones with α‑Diazomethylphosphonate Mediated by a Chiral Silver SPINOL Phosphate Catalyst %U https://acs.figshare.com/articles/journal_contribution/Formal_Asymmetric_Cycloaddition_of_Activated_-Unsaturated_Ketones_with_Diazomethylphosphonate_Mediated_by_a_Chiral_Silver_SPINOL_Phosphate_Catalyst/7579775 %R 10.1021/acs.orglett.8b03436.s001 %2 https://acs.figshare.com/ndownloader/files/14077676 %K diazomethyl %K functionalized %K ee %K density %K M 11 calculations %K Mediated %K nonspiro-phosphonyl %K cycloaddition %K Formal Asymmetric Cycloaddition %K Diazomethylphosphonate %K mechanism %K method %K stereoselectivitie %K dipolar %K Chiral Silver SPINOL Phosphate Catalyst %K Ketone %K Activated %K nitrile electron-withdrawing group %K yield %K ketone %K chiral silver phosphate catalyst %K acyclic %K α- %K Unsaturated %X 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% ee, 99:1 dr) and yields (up to 95%). A stepwise mechanism is proposed based upon density functional M11 calculations. %I ACS Publications