Synthesis and reactions of amino acid-derived benziodazole oxides: New chiral oxidizing reagents

Viktor V. Zhdankin, Jason T. Smart, Peng Zhao, Paul Kiprof

Research output: Contribution to journalArticlepeer-review

65 Scopus citations

Abstract

The novel benziodazole oxides (3) can be prepared by oxidation of the readily available 2-iodobenzamides (5 or 6) with potassium bromate. Benziodazole oxides can find practical application as selective oxidizing reagents analogous to the widely used Dess-Martin periodinane (1) and benziodoxole oxide (2). Preliminary results indicate that reagents 3 can oxidize primary alcohols to aldehydes, while non-symmetric sulfides are oxidized to chiral sulfoxides with moderate enantioselectivity.

Original languageEnglish (US)
Pages (from-to)5299-5302
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number28
DOIs
StatePublished - Jul 8 2000

Bibliographical note

Funding Information:
This work was supported by a research grant from the National Science Foundation (NSF/CHE-9802823). We would also like to thank the Minnesota Supercomputer Institute and the UMD Digital Imaging Laboratory (DIL) for a generous allocation of computer resources.

Fingerprint

Dive into the research topics of 'Synthesis and reactions of amino acid-derived benziodazole oxides: New chiral oxidizing reagents'. Together they form a unique fingerprint.

Cite this