Biotin – The Chiral Challenge
DOI:
https://doi.org/10.2533/chimia.2009.265Keywords:
Asymmetric hydrogenation, Cyclic anhydrides, Dream reaction, Homogeneous catalysis, VitaminsAbstract
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.Downloads
Published
2009-05-27
Issue
Section
Scientific Articles
License
Copyright (c) 2009 Swiss Chemical Society
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
How to Cite
[1]
Chimia 2009, 63, 265, DOI: 10.2533/chimia.2009.265.