Valinol is an
organic compound named after, and commonly produced from, the
amino acid valine. The compound is
chiral and is produced almost exclusively as the S‑isomer (also designated as the L‑isomer), due to the abundant supply of S-valine. It is part of a broader class of
amino alcohols.
Synthesis
Valinol can be generated by converting the carboxylic group of valine to an alcohol with a strong
reducing agent such as
lithium aluminium hydride
Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li Al H4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic ...
, or with
NaBH4 and
I2 (forming the
borane–tetrahydrofuran
Borane–tetrahydrofuran is a dipolar bond charge-transfer complex composed of borane and tetrahydrofuran (THF). These solutions are used for reductions and hydroboration, reactions that are useful in synthesis of organic compounds.Marek Zaidlewi ...
complex). In both cases the valinol produced can be subsequently purified by
short path distillation.
Reactions
Valinol is mainly used to prepare chiral
oxazolines, a process which can be achieved via a
variety of methods. These oxazolines are principally used as
ligands in
asymmetric catalysis.
[{{cite journal, last=McManus, first=Helen A., author2=Guiry, Patrick J. , title=Recent Developments in the Application of Oxazoline-Containing Ligands in Asymmetric Catalysis, journal=Chemical Reviews, volume=104, issue=9, pages=4151–4202, doi=10.1021/cr040642v, pmid=15352789, date=Sep 2004]
See also
*
(S)-iPr-PHOX - an oxazoline ligand made using valinol
References
Ligands
Primary alcohols
Amino alcohols