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

Paul M. O'Neill; Stephen Hindley; Matthew D. Pugh; Jill Davies; Patrick G. Bray; B. Kevin Park; Dauda S. Kapu; Steve Ward; Paul A. Stocks

doi:10.1016/j.tetlet.2003.09.033

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

Paul M. O'Neill
, Stephen Hindley
, Matthew D. Pugh
, Jill Davies
, Patrick G. Bray
, B. Kevin Park
, Dauda S. Kapu
, Steve Ward
, Paul A. Stocks

Tropical Disease Biology

Research output: Contribution to journal › Article › peer-review

71 Citations (Scopus)

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.

Original language	English
Pages (from-to)	8135-8138
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	44
DOIs	https://doi.org/10.1016/j.tetlet.2003.09.033
Publication status	Published - 27 Oct 2003

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O'Neill, P. M., Hindley, S., Pugh, M. D., Davies, J., Bray, P. G., Park, B. K., Kapu, D. S., Ward, S., & Stocks, P. 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, 44(44), 8135-8138. https://doi.org/10.1016/j.tetlet.2003.09.033

@article{07ef8ea9fcdc44139ef8ee4bdec4df2b,

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

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.",

author = "O'Neill, \{Paul M.\} and Stephen Hindley and Pugh, \{Matthew D.\} and Jill Davies and Bray, \{Patrick G.\} and Park, \{B. Kevin\} and Kapu, \{Dauda S.\} and Steve Ward and Stocks, \{Paul A.\}",

year = "2003",

month = oct,

day = "27",

doi = "10.1016/j.tetlet.2003.09.033",

language = "English",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Co(thd)(2): a superior catalyst for aerobic epoxidation and hydroperoxysilylation of unactivated alkenes: application to the synthesis of spiro-1,2,4-trioxanes

AU - O'Neill, Paul M.

AU - Hindley, Stephen

AU - Pugh, Matthew D.

AU - Davies, Jill

AU - Bray, Patrick G.

AU - Park, B. Kevin

AU - Kapu, Dauda S.

AU - Ward, Steve

AU - Stocks, Paul A.

PY - 2003/10/27

Y1 - 2003/10/27

N2 - 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.

AB - 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.

U2 - 10.1016/j.tetlet.2003.09.033

DO - 10.1016/j.tetlet.2003.09.033

M3 - Article

SN - 0040-4039

VL - 44

SP - 8135

EP - 8138

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 44

ER -

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

Abstract

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