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

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

doi:10.1016/S0040-4039(00)00836-4

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

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

Chemistry & Biochemistry

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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 language	English (US)
Pages (from-to)	5299-5302
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	28
DOIs	https://doi.org/10.1016/S0040-4039(00)00836-4
State	Published - 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.

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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.",

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AU - Zhdankin, Viktor V.

AU - Smart, Jason T.

AU - Zhao, Peng

AU - Kiprof, Paul

N1 - 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.

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AB - 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.

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

Abstract

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