Sequential- and tandem-oxidation-epoxidation reactions employing guanidine bases

David J. Phillips; Joseline L. Kean; Andrew E. Graham

doi:10.1016/j.tet.2013.05.036

Sequential- and tandem-oxidation-epoxidation reactions employing guanidine bases

David J. Phillips, Joseline L. Kean, Andrew E. Graham^*

^*Corresponding author for this work

Faculty of Computing, Engineering and Science

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

5 Citations (Scopus)

Abstract

1,5,7-Triazabicyclo[4.4.0]dec-1-ene (TBD) and 7-methyl-1,5,7- triazabicyclo[4.4.0]dec-1-ene (MTBD) promote the efficient formation of sulfonium ylides from sulfonium salts in the Corey-Chaykovsky epoxidation of aldehydes and provide excellent yields of the corresponding epoxides. This reaction protocol can be further adapted to allow for the development of both sequential and tandem-oxidation-epoxidation protocols from aldehydes generated in situ by manganese dioxide (MnO₂) or barium manganate (BaMnO ₄) mediated oxidation reactions.

Original language	English
Pages (from-to)	6196-6202
Number of pages	7
Journal	Tetrahedron Letters
Volume	69
Issue number	30
DOIs	https://doi.org/10.1016/j.tet.2013.05.036
Publication status	Published - 29 Jul 2013

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10.1016/j.tet.2013.05.036Licence: CC BY-NC-ND

5 Citations
1 Doctoral Thesis

Application of Tandem Oxidation Processes to the Synthesis of Novel Oxabicycloalkane Protein Phosphatase Inhibitors
Phillips, D., 2007
Research output: Types of Thesis › Doctoral Thesis

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title = "Sequential- and tandem-oxidation-epoxidation reactions employing guanidine bases",

abstract = "1,5,7-Triazabicyclo[4.4.0]dec-1-ene (TBD) and 7-methyl-1,5,7- triazabicyclo[4.4.0]dec-1-ene (MTBD) promote the efficient formation of sulfonium ylides from sulfonium salts in the Corey-Chaykovsky epoxidation of aldehydes and provide excellent yields of the corresponding epoxides. This reaction protocol can be further adapted to allow for the development of both sequential and tandem-oxidation-epoxidation protocols from aldehydes generated in situ by manganese dioxide (MnO2) or barium manganate (BaMnO 4) mediated oxidation reactions. ",

author = "Phillips, {David J.} and Kean, {Joseline L.} and Graham, {Andrew E.}",

year = "2013",

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day = "29",

doi = "10.1016/j.tet.2013.05.036",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Sequential- and tandem-oxidation-epoxidation reactions employing guanidine bases

AU - Phillips, David J.

AU - Kean, Joseline L.

AU - Graham, Andrew E.

PY - 2013/7/29

Y1 - 2013/7/29

N2 - 1,5,7-Triazabicyclo[4.4.0]dec-1-ene (TBD) and 7-methyl-1,5,7- triazabicyclo[4.4.0]dec-1-ene (MTBD) promote the efficient formation of sulfonium ylides from sulfonium salts in the Corey-Chaykovsky epoxidation of aldehydes and provide excellent yields of the corresponding epoxides. This reaction protocol can be further adapted to allow for the development of both sequential and tandem-oxidation-epoxidation protocols from aldehydes generated in situ by manganese dioxide (MnO2) or barium manganate (BaMnO 4) mediated oxidation reactions.

AB - 1,5,7-Triazabicyclo[4.4.0]dec-1-ene (TBD) and 7-methyl-1,5,7- triazabicyclo[4.4.0]dec-1-ene (MTBD) promote the efficient formation of sulfonium ylides from sulfonium salts in the Corey-Chaykovsky epoxidation of aldehydes and provide excellent yields of the corresponding epoxides. This reaction protocol can be further adapted to allow for the development of both sequential and tandem-oxidation-epoxidation protocols from aldehydes generated in situ by manganese dioxide (MnO2) or barium manganate (BaMnO 4) mediated oxidation reactions.

U2 - 10.1016/j.tet.2013.05.036

DO - 10.1016/j.tet.2013.05.036

M3 - Article

AN - SCOPUS:84878927733

SN - 0040-4039

VL - 69

SP - 6196

EP - 6202

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 30

ER -

Sequential- and tandem-oxidation-epoxidation reactions employing guanidine bases

Abstract

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Research output

Application of Tandem Oxidation Processes to the Synthesis of Novel Oxabicycloalkane Protein Phosphatase Inhibitors

Cite this