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A practical synthesis of enantiopure (S)-4-(4-hydroxybenzyl)-oxazolidin-2-one

✍ Scribed by Rachel Green; Piers J.M. Taylor; Steven D. Bull; Tony D. James; Mary F. Mahon; Andy T. Merritt

Book ID
104359967
Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
177 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

A high yielding four-step synthesis of enantiopure 4-(4-hydroxybenzyl)-oxazolidin-2-one (S)-1 from N-Boc-L-tyrosine is described. (S)-1 is a key intermediate for the preparation of a number of polymer supported Evans' oxazolidin-2-ones that have been employed previously for solid supported asymmetric synthesis.

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A Practical Synthesis of Enantiopure (R)
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## Abstract The title compound __R__‐4a was prepared from (–)‐quinic acid (1) in 6 steps in 18% overall yield (Scheme 3) and with 100% enantiomeric purity (Figure 1). The initiating step is the regio‐ and stereoselective acetalization of the __trans__‐oriented vicinal OH groups of 1 (+ 5 β†’ 8). Alco