%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