Synthesis of Methoxyisopropyl (MIP)-Protected (R)-Mandelonitrile and Derivatives in a Flow Reactor

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 transforma...

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Bibliographic Details
Published inJournal of flow chemistry Vol. 2; no. 4; pp. 124 - 128
Main Authors Delville, Mariëlle M. E., van Gool, Jasper J. F., van Wijk, Ivo M., van Hest, Jan C. M., Rutjes, Floris P. J. T.
Format Journal Article
LanguageEnglish
Published Cham Springer International Publishing 13.12.2012
Subjects
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Green Chemistry
Industrial Chemistry/Chemical Engineering
Inorganic Chemistry
Nanochemistry
Organic Chemistry
reaction optimization
microreactor
MIP-protection
mandelonitrile
flow chemistry
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Summary: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.
ISSN:2062-249X
2063-0212
DOI:10.1556/JFC-D-12-00008