The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis
One of the biggest challenges in asymmetric synthesis is to prevent racemization of enantiopure starting materials. However, at least some of the enantiopurity is lost in most of the existing reactions used in synthetic organic chemistry. This translates into unnecessary material losses. Naturally e...
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| Format: | Article |
| Language: | English |
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MDPI AG
2010-09-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/15/9/6512/ |
| _version_ | 1811251272305606656 |
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| author | Ari M. P. Koskinen Essi J. Karppanen |
| author_facet | Ari M. P. Koskinen Essi J. Karppanen |
| author_sort | Ari M. P. Koskinen |
| collection | DOAJ |
| description | One of the biggest challenges in asymmetric synthesis is to prevent racemization of enantiopure starting materials. However, at least some of the enantiopurity is lost in most of the existing reactions used in synthetic organic chemistry. This translates into unnecessary material losses. Naturally enantiopure proteinogenic amino acids that can be transformed into many useful intermediates in drug syntheses, for example, are especially vulnerable to this. The phenylfluoren-9-yl (Pf) group, a relatively rarely used protecting group, has proven to be able to prevent racemization in α-amino compounds. This review article showcases the use of Pf-protected amino acid derivatives in enantiospecific synthesis. |
| first_indexed | 2024-04-12T16:17:07Z |
| format | Article |
| id | doaj.art-229a81e410bb4f2998adb5079a402194 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-12T16:17:07Z |
| publishDate | 2010-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-229a81e410bb4f2998adb5079a4021942022-12-22T03:25:41ZengMDPI AGMolecules1420-30492010-09-011596512654710.3390/molecules15096512The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific SynthesisAri M. P. KoskinenEssi J. KarppanenOne of the biggest challenges in asymmetric synthesis is to prevent racemization of enantiopure starting materials. However, at least some of the enantiopurity is lost in most of the existing reactions used in synthetic organic chemistry. This translates into unnecessary material losses. Naturally enantiopure proteinogenic amino acids that can be transformed into many useful intermediates in drug syntheses, for example, are especially vulnerable to this. The phenylfluoren-9-yl (Pf) group, a relatively rarely used protecting group, has proven to be able to prevent racemization in α-amino compounds. This review article showcases the use of Pf-protected amino acid derivatives in enantiospecific synthesis.http://www.mdpi.com/1420-3049/15/9/6512/phenylfluorenylamino acidnitrogen protecting groupenantiospecificenantiopure |
| spellingShingle | Ari M. P. Koskinen Essi J. Karppanen The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis Molecules phenylfluorenyl amino acid nitrogen protecting group enantiospecific enantiopure |
| title | The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis |
| title_full | The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis |
| title_fullStr | The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis |
| title_full_unstemmed | The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis |
| title_short | The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis |
| title_sort | 9 phenyl 9 fluorenyl group for nitrogen protection in enantiospecific synthesis |
| topic | phenylfluorenyl amino acid nitrogen protecting group enantiospecific enantiopure |
| url | http://www.mdpi.com/1420-3049/15/9/6512/ |
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