A General Method for the Synthesis of Enantiopure 1,5-Amino Alcohols

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 pheny...

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Bibliographic Details
Published in:European journal of organic chemistry 2016-02, Vol.2016 (4), p.693-703
Main Authors: Guignard, Guillaume, Llor, Núria, Urbina, Aina, Bosch, Joan, Amat, Mercedes
Format: Article
Language:English
Subjects:
Amino alcohols
Asymmetric synthesis
Lactames
Lactams
Organic synthesis
Reducció química
Reduction
Reduction (Chemistry)
Ring opening
Synthetic methods
Síntesi asimètrica
Síntesi orgànica
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Summary: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. A general method for the synthesis of diversely substituted enantiopure 5‐amino‐1‐pentanols is described. The key step is an LiNH2BH3‐promoted reductive opening of (R)‐phenylglycinol‐derived oxazolopiperidone lactams.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201501409