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Co(thd)(2): a superior catalyst for aerobic epoxidation and hydroperoxysilylation of unactivated alkenes: application to the synthesis of spiro-1,2,4-trioxanes

O'Neill, Paul M., Hindley, Stephen, Pugh, Matthew D., Davies, Jill, Bray, Patrick, Park, B. Kevin, Kapu, Dauda S., Ward, Stephen ORCID: https://orcid.org/0000-0003-2331-3192 and Stocks, Paul A. (2003) 'Co(thd)(2): a superior catalyst for aerobic epoxidation and hydroperoxysilylation of unactivated alkenes: application to the synthesis of spiro-1,2,4-trioxanes'. Tetrahedron Letters, Vol 44, Issue 44, pp. 8135-8138.

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Abstract

Bis(2,2;6,6-tetramethyl-3,5-heptanedionato)cobalt(II) (Co(thd)(2)), a beta-diketonate prepared in a simple one-step procedure, is an excellent catalyst for aerobic epoxidation and Mukaiyama-Isayama hydroperoxysilylation of unactivated alkenes. For hydroperoxysilylation, Co(thd)(2) is superior to Co(acac)(2) and can catalyse oxidation of cyclic alkenes in excellent yield. Chiral beta-diketonate or keto iminato catalysts failed to catalyse this reaction in an enantioselective manner and a free radical mechanism consistent with this observation is proposed. Hydroperoxysilylation of cyclohex-1-enylmethanol by Co(thd)(2) followed by addition of a ketone/TsOH provides a simple one-pot procedure for the synthesis of spiro-1,2,4-trioxane antimalarials. (C) 2003 Published by Elsevier Ltd.

Item Type: Article
Additional Information: Times Cited: 23
Subjects: QV Pharmacology > Anti-Inflammatory Agents. Anti-Infective Agents. Antineoplastic Agents > QV 256 Antimalarials
QV Pharmacology > QV 34 Experimental pharmacology (General)
Faculty: Department: Groups (2002 - 2012) > Molecular & Biochemical Parasitology Group
Digital Object Identifer (DOI): https://doi.org/10.1016/j.tetlet.2003.09.033
Depositing User: Ms Julia Martin
Date Deposited: 25 Jul 2012 11:25
Last Modified: 06 Feb 2018 13:04
URI: https://archive.lstmed.ac.uk/id/eprint/2638

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