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Title: A general method for the synthesis of enantiopure 1,5-amino alcohols
Author: Guignard, Guillaume
Llor Brunés, Núria
Urbina Teixidor, Aina
Bosch Cartes, Joan
Amat Tusón, Mercedes
Keywords: Síntesi orgànica
Síntesi asimètrica
Reducció química
Organic synthesis
Asymmetric synthesis
Reduction (Chemistry)
Issue Date: Feb-2016
Publisher: Wiley-VCH
Abstract: A variety of (R)-phenylglycinol-derived oxazolopiperidone lactams 1-14 were converted to linear-chain enantiopure amino diols 15-26 by reduction with LiNH2BH3 in an unprecedented process involving the simultaneous reductive opening of the oxazolidine and lactam rings. Subsequent removal of the phenylethanol moiety gave enantiopure 5-amino-1-pentanols bearing substituents at the 2-, 3-, 4-, 2,2-, 2,3- 2,4- and 3,4-positions (28-36), which were isolated as their N-Boc derivatives.
Note: Versió postprint del document publicat a:
It is part of: European Journal of Organic Chemistry, 2016, vol. 2016, num. 4, p. 693-703
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ISSN: 1434-193X
Appears in Collections:Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Institut de Biomedicina (IBUB))

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