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Synthesis of (R)-tert-Leucinol by Classical Resolution of the Racemic Mixture

✍ Scribed by Prof. Karlheinz Drauz; Wilfried Jahn; Dr. Michael Schwarm

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
385 KB
Volume
1
Category
Article
ISSN
0947-6539

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✦ Synopsis

Optically active tert-leucinol is an important building block in asymmetric synthesis. However, the ( R ) enantiomer particularly has so far remained difticult to obtain, mainly because of the laborious synthesis of the precursor amino acid, (R)-tertleucine. Here we present a new, classical resolution of racemic tert-leucinol, which allows straightforward preparation of each, but especially the ( R ) enantiomer, in good yields and high optical purities. The feasibility of the synthesis of useful derivatives is demonstrated by transformation into the corresponding (R)-4-tert-butyl-2-oxazolidinone.

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## Abstract The resolution of racemates through their diastereomeric salts can be positively affected by the addition of small amounts of suitable nucleation inhibitors. This discovery is a logical extension of β€œDutch Resolution”, in which equimolar amounts of resolving agents that are members of t