Diastereodivergent and Enantioselective Access to
Spiroepoxides via Organocatalytic Epoxidation of Unsaturated Pyrazolones
Posted on 2017-09-14 - 14:33
Readily
available chiral amine–thioureas are effective catalysts
for the first diastereo- and enantioselective epoxidation of unsaturated
pyrazolones. The trans- or cis-spiroepoxides
are preferentially obtained in good yield and high to excellent enantioselectivity
using an appropriate organocatalyst and tert-butyl
hydroperoxide as the oxidant. The epoxidation appears applicable to
highly challenging β,β′-substituted unsaturated
pyrazolones, giving access to spiroepoxides bearing two vicinal quaternary
stereocenters. The reaction represents a unique example of Weitz–Scheffer
epoxidation, where the catalyst-controlled ring-closure step is usefully
exploited to prepare both enantioenriched diastereomeric epoxides.
CITE THIS COLLECTION
DataCite
3 Biotech
3D Printing in Medicine
3D Research
3D-Printed Materials and Systems
4OR
AAPG Bulletin
AAPS Open
AAPS PharmSciTech
Abhandlungen aus dem Mathematischen Seminar der Universität Hamburg
ABI Technik (German)
Academic Medicine
Academic Pediatrics
Academic Psychiatry
Academic Questions
Academy of Management Discoveries
Academy of Management Journal
Academy of Management Learning and Education
Academy of Management Perspectives
Academy of Management Proceedings
Academy of Management Review
Meninno, Sara; Roselli, Angelo; Capobianco, Amedeo; Overgaard, Jacob; Lattanzi, Alessandra (2017). Diastereodivergent and Enantioselective Access to
Spiroepoxides via Organocatalytic Epoxidation of Unsaturated Pyrazolones. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b02189
or
Select your citation style and then place your mouse over the citation text to select it.
SHARE
Usage metrics
Read the peer-reviewed publication
AUTHORS (5)
SM
Sara Meninno
AR
Angelo Roselli
AC
Amedeo Capobianco
JO
Jacob Overgaard
AL
Alessandra Lattanzi