Arylboronic Acid-Catalyzed C-Allylation of Unprotected Oximes: Total Synthesis of N-Me-Euphococcine

Juha H Siitonen; Padmanabha V Kattamuri; Muhammed Yousufuddin; László Kürti

doi:10.1021/acs.orglett.0c00727

Arylboronic Acid-Catalyzed C-Allylation of Unprotected Oximes: Total Synthesis of N-Me-Euphococcine

Org Lett. 2020 Mar 20;22(6):2486-2489. doi: 10.1021/acs.orglett.0c00727. Epub 2020 Mar 11.

Authors

Juha H Siitonen¹, Padmanabha V Kattamuri¹, Muhammed Yousufuddin², László Kürti¹

Affiliations

¹ Department of Chemistry, Rice University, 6500 Main Street, Houston, Texas 77030, United States.
² Life and Health Sciences Department, The University of North Texas at Dallas, 7400 University Hills Boulevard, Dallas, Texas 75241, United States.

PMID: 32159964
DOI: 10.1021/acs.orglett.0c00727

Abstract

O-Unprotected keto- and aldoximes are readily C-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly substituted N-α-secondary and tertiary homoallylic hydroxylamines. The method was used in the total synthesis of the trace alkaloid N-Me-Euphococcine.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Alkaloids / chemical synthesis*
Allyl Compounds / chemistry*
Boronic Acids / chemistry*
Catalysis
Hydroxylamines / chemistry
Oximes / chemistry*

Substances

Alkaloids
Allyl Compounds
Boronic Acids
Hydroxylamines
Oximes

Grants and funding

R01 GM114609/GM/NIGMS NIH HHS/United States