Synthetic approaches to a chiral 4-amino-3-hydroxy piperidine with pharmaceutical relevance
Four synthetic strategies were evaluated towards the preparation of (-)-(3R,4R)-1-benzyl-4-(benzylamino)piperidin-3-ol (1), which was constructed with control over the relative and absolute stereochemistry of the 4,3-amino alcohol moiety. The first strategy employed a novel Rh(I) catalyzed asymmetri...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2012-07, Vol.10 (27), p.5253-5257 |
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| container_end_page | 5257 |
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| container_issue | 27 |
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| container_title | Organic & biomolecular chemistry |
| container_volume | 10 |
| creator | Ortiz, Adrian Young, Ian S Sawyer, James R Hsiao, Yi Singh, Amarjit Sugiyama, Masano Corbett, R Michael Chau, Melissa Shi, Zhongping Conlon, David A |
| description | Four synthetic strategies were evaluated towards the preparation of (-)-(3R,4R)-1-benzyl-4-(benzylamino)piperidin-3-ol (1), which was constructed with control over the relative and absolute stereochemistry of the 4,3-amino alcohol moiety. The first strategy employed a novel Rh(I) catalyzed asymmetric hydrogenation, while two other strategies exploited the existing stereochemistry in 2-deoxy-D-ribose, and the fourth explored both biocatalytic and classical resolution techniques as a means to impart enantioenrichment to racemic intermediates en route to targeted structure (-)-1. |
| doi_str_mv | 10.1039/c2ob25411e |
| format | Article |
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| fulltext | fulltext |
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| ispartof | Organic & biomolecular chemistry, 2012-07, Vol.10 (27), p.5253-5257 |
| issn | 1477-0520 1477-0539 |
| language | eng |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Hydrogenation Models, Molecular Molecular Structure Piperidines - chemical synthesis Stereoisomerism |
| title | Synthetic approaches to a chiral 4-amino-3-hydroxy piperidine with pharmaceutical relevance |
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