- Title
- A ring-closing metathesis approach to eight-membered benzannelated scaffolds and subsequent internal alkene isomerizations
- Creator
- Taher, Abu
- Creator
- Aderibigbe, Blessing A
- Creator
- Morgans, Garreth L
- Creator
- Madeley, Lee G
- Creator
- Khanye, Setshaba D
- Creator
- Van der Westhuizen, Leandi
- Creator
- Fernandes, Manuel A
- Creator
- Smith, Vincent J
- Creator
- Michael, Joseph P
- Creator
- Green, Ivan R
- Creator
- Van Otterlo, Willem A L
- Date Issued
- 2013
- Date
- 2013
- Type
- text
- Type
- article
- Identifier
- http://hdl.handle.net/10962/66252
- Identifier
- vital:28925
- Identifier
- https://doi.org/10.1016/j.tet.2012.12.043
- Description
- publisher version
- Description
- A set of eight-membered benzannelated heterocycles containing two heteroatoms (O,O, NR,NR and O,NR where R=protecting group) was synthesized by ring-closing metathesis from the corresponding ortho-bis-allyl precursors. In this manner, 7-methoxy-2,5-dihydro-1,6-benzodioxocine, 1,2,5,6-tetrahydro-1,6-benzodiazocines, 5,6-dihydro-2H-1,6-benzoxazocines and 5,6,9,10-tetrahydropyrido[2,3-b][1,4]diazocine were synthesized. A number of these compounds were then treated with the catalyst [RuClH(CO)(PPh3)3] to facilitate isomerization of the alkene into conjugation with the heteroatoms in the eight-membered ring. Quite surprisingly, an equal ratio of regioisomers was obtained, even if the heteroatoms were different.
- Format
- 10 pages
- Format
- Language
- English
- Relation
- Tetrahedron
- Relation
- Taher, Abu, Aderibigbe, Blessing A., Morgans, Garreth L., Madeley, Lee G., Khanye, Setshaba D., Van der Westhuizen, Leandi, Fernandes, Manuel A., Smith, Vincent J., Michael, Joseph P., Green, Ivan R., Van Otterlo, Willem A.L. (2013) A ring-closing metathesis approach to eight-membered benzannelated scaffolds and subsequent internal alkene isomerizations. Tetrahedron, 69 (8). p. 2038 – 2047. ISSN:0040-4020. https://doi.org/10.1016/j.tet.2012.12.043
- Relation
- Tetrahedron volume 69 number 2038 2047 88 February 2013 0040-4020
- Rights
- Elsevier B.V.
- Rights
- Use of this resource is governed by the terms and conditions of the Tetrahedron Open Access Options Statement (https://www.elsevier.com/journals/tetrahedron/0040-4020/open-access-options)
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Khanye, David Setshaba (Associate Prof)
RU Department of Chemistry
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