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Cyanohydrins are synthetically versatile chiral building blocks in organic synthesis. They can be conveniently synthesized in enantiomerically pure form via chemoenzymatic hydrogen cyanide addition onto the corresponding aldehyde using hydroxynitrile lyase.
Recently, we reported that such transformations can be efficiently carried out in a continuous flow manner using microreactors. Since racemization of enantiopure cyanohydrins occurs readily under slightly basic conditions, they should be protected before the follow-up reactions, preferably under acidic conditions.
In this contribution, we demonstrate that the methoxyisopropyl protection of mandelonitrile can be conveniently optimized in an automated microscale continuous flow system and subsequently scaled up under the same conditions by applying a larger flow reactor.
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Synthesis of Methoxyisopropyl (MIP)-Protected (R)-Mandelonitrile and Derivatives in a Flow Reactor
http://www.akademiai.com/content/9488206462627n38/?p=6ed413d7b9fb47fe9fe7e1262c37694f&pi=2
| Journal of Flow Chemistry | |
| Publisher | Akadémiai Kiadó |
| ISSN | 2062-249X (Print) 2063-0212 (Online) |
| Subject | Flow Chemistry |
| Issue | Volume 2, Number 4/December 2012 |
| Pages | 124-128 |
| DOI | 10.1556/JFC-D-12-00008 |
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Authors
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f.rutjes@science.ru.nl1Institute for Molecules and Materials Radboud University Nijmegen Heyendaalseweg 135 6525 AJ Nijmegen the Netherlands
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Floris P.J.T. Rutjes
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The IMM-office is located on the 3rd floor of the Huygens building, which is at walking distance (about 5 min.) from the railway station Nijmegen Heyendaal.
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