ol8b03436_si_001.pdf (12.34 MB)
Formal Asymmetric Cycloaddition of Activated α,β-Unsaturated Ketones with α‑Diazomethylphosphonate Mediated by a Chiral Silver SPINOL Phosphate Catalyst
journal contribution
posted on 2019-01-11, 19:19 authored by Bo Zheng, Haohua Chen, Lei Zhu, Xiqiang Hou, Yan Wang, Yu Lan, Yungui PengAn
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.
History
Usage metrics
Categories
Keywords
diazomethylfunctionalizedeedensityM 11 calculationsMediatednonspiro-phosphonylcycloadditionFormal Asymmetric CycloadditionDiazomethylphosphonatemechanismmethodstereoselectivitiedipolarChiral Silver SPINOL Phosphate CatalystKetoneActivatednitrile electron-withdrawing groupyieldketonechiral silver phosphate catalystacyclicα-Unsaturated
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC