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Biotin – The Chiral Challenge
- Source :
- CHIMIA, Vol 63, Iss 5 (2009)
- Publication Year :
- 2009
- Publisher :
- Swiss Chemical Society, 2009.
-
Abstract
- In this contribution, the first examples of the catalytic highly enantioselective reduction of cyclic meso-anhydrides to lactones and of thioanhydrides to thiolactones are described. The N-benzyl protected key building blocks in the industrial synthesis of (+)-biotin were so far only accessible by usage of expensive reagents in multi-step procedures. In contrast, homogeneous catalytic enantioselective hydrogenation of the corresponding meso-anhydride mediated by a metal phosphane complex proceeds with high optical induction (ee >95%) and excellent yield. The catalytic system provides a generally applicable new method for the preparation of lactones from cyclic anhydrides.
Details
- Language :
- German, English, French
- ISSN :
- 00094293 and 26732424
- Volume :
- 63
- Issue :
- 5
- Database :
- Directory of Open Access Journals
- Journal :
- CHIMIA
- Publication Type :
- Academic Journal
- Accession number :
- edsdoj.29f00b286f5c41e99b6bd9c39d92125a
- Document Type :
- article
- Full Text :
- https://doi.org/10.2533/chimia.2009.265