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Enantioselective synthesis of benzylic stereocentres via Claisen rearrangement of enantiomerically pure allylic alcohols: preparation of (R)- and (S)-3-methyl-2-phenylbutylamine

✍ Scribed by Elisabetta Brenna; Claudio Fuganti; Francesco G. Gatti; Massimo Passoni; Stefano Serra

Book ID: 104359953
Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 145 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(03)00454-3

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✦ Synopsis

The Johnson-Claisen rearrangement of enantiopure allylic alcohols in triethylorthopropionate is the key step for the preparation of chiral molecules with benzylic stereogenic carbon atoms bearing an isopropyl moiety. The synthetic procedure is applied to the preparation of (R)-and (S)-3-methyl-2-phenylbutylamine.

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