Cyclobutane serine amino acid derivatives as 5-hydroxyproline precursors
This article is dedicated to Professor Benito Alcaide on the occasion of his 60 th birthday
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| Main Authors: | , , , , |
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| Format: | artículo biblioteca |
| Language: | English |
| Published: |
2009-06-10
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| Subjects: | 5-Hydroxyproline, Cyclobutane derivatives, Michael addition, Wittig reaction, |
| Online Access: | http://hdl.handle.net/10261/47868 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003339 |
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dig-icvv-es-10261-478682016-02-17T09:10:17Z Cyclobutane serine amino acid derivatives as 5-hydroxyproline precursors Pérez-Fernández, Marta Avenoza, Alberto Busto, Jesús H. Peregrina, Jesús M. Rodríguez, Fernando Ministerio de Educación y Ciencia (España) Gobierno de La Rioja European Commission Consejo Superior de Investigaciones Científicas (España) 5-Hydroxyproline Cyclobutane derivatives Michael addition Wittig reaction This article is dedicated to Professor Benito Alcaide on the occasion of his 60 th birthday The synthesis of the 5-hydroxyproline derivatives 3a and 3b using cyclobutane serine analogs 1 and 2 as starting materials is reported. This process occurs with moderate cis/trans selectivity. A mechanism for this reaction is also proposed. Cyclobutane serine analog 1 was tested in tandem Michael and Wittig-like reactions, providing some evidence of the mechanism proposed. We are grateful to the Ministerio de Educación y Ciencia (project CTQ2006-05825/BQU). M. P. -F. also thanks the Gobierno de La Rioja for her doctoral fellowship. F. R. thanks the C.S.I.C. for his JAE-Doc Program contract. Peer reviewed 2012-04-03T09:36:05Z 2012-04-03T09:36:05Z 2009-06-10 artículo http://purl.org/coar/resource_type/c_6501 ARKIVOC - Online Journal of Organic Chemistry 191-2002 (2009) 1551-7004 http://hdl.handle.net/10261/47868 1551-7012 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003339 en http://www.arkat-usa.org/arkivoc-journal/browse-arkivoc/2010/3/ open |
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España |
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ES |
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| databasecode |
dig-icvv-es |
| tag |
biblioteca |
| region |
Europa del Sur |
| libraryname |
Biblioteca del ICVV España |
| language |
English |
| topic |
5-Hydroxyproline Cyclobutane derivatives Michael addition Wittig reaction 5-Hydroxyproline Cyclobutane derivatives Michael addition Wittig reaction |
| spellingShingle |
5-Hydroxyproline Cyclobutane derivatives Michael addition Wittig reaction 5-Hydroxyproline Cyclobutane derivatives Michael addition Wittig reaction Pérez-Fernández, Marta Avenoza, Alberto Busto, Jesús H. Peregrina, Jesús M. Rodríguez, Fernando Cyclobutane serine amino acid derivatives as 5-hydroxyproline precursors |
| description |
This article is dedicated to Professor Benito Alcaide on the occasion of his 60
th
birthday |
| author2 |
Ministerio de Educación y Ciencia (España) |
| author_facet |
Ministerio de Educación y Ciencia (España) Pérez-Fernández, Marta Avenoza, Alberto Busto, Jesús H. Peregrina, Jesús M. Rodríguez, Fernando |
| format |
artículo |
| topic_facet |
5-Hydroxyproline Cyclobutane derivatives Michael addition Wittig reaction |
| author |
Pérez-Fernández, Marta Avenoza, Alberto Busto, Jesús H. Peregrina, Jesús M. Rodríguez, Fernando |
| author_sort |
Pérez-Fernández, Marta |
| title |
Cyclobutane serine amino acid derivatives as 5-hydroxyproline precursors |
| title_short |
Cyclobutane serine amino acid derivatives as 5-hydroxyproline precursors |
| title_full |
Cyclobutane serine amino acid derivatives as 5-hydroxyproline precursors |
| title_fullStr |
Cyclobutane serine amino acid derivatives as 5-hydroxyproline precursors |
| title_full_unstemmed |
Cyclobutane serine amino acid derivatives as 5-hydroxyproline precursors |
| title_sort |
cyclobutane serine amino acid derivatives as 5-hydroxyproline precursors |
| publishDate |
2009-06-10 |
| url |
http://hdl.handle.net/10261/47868 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003339 |
| work_keys_str_mv |
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1777670836351664128 |