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Tellurium: Use in the synthesis of allylic amines from 5-hydroxymethyl-2-oxazolidinones

โœ Scribed by Qinyu Xu; Donald C. Dittmer

Book ID
104261015
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
271 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Non-racemic or racemic allylic amines are obtained by treatment of sulfonate esters of 5hydroxymethyl-2-oxazolidinones with telluride ion.

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Asymmetric desymmetrization of 2-[(etR)-et-methylbenzyl]amino-1,3-propanediol (1) with 2-chloroethyl chloroformate and DBU at room temperature gave optically active (4S)-4-hydroxymethyl-N-[(otR)-ot-methylbenzyl]-2-oxazolidinone [(4S)-2] (up to 94% de). This reaction involves kinetic resolution and [