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A General Method for the Synthesis of Enantiopure 1,5‐Amino Alcohols
Author(s) -
Guignard Guillaume,
Llor Núria,
Urbina Aina,
Bosch Joan,
Amat Mercedes
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501409
Subject(s) - enantiopure drug , chemistry , moiety , oxazolidine , stereochemistry , enantioselective synthesis , organic chemistry , catalysis
A variety of ( R )‐phenylglycinol‐derived oxazolopiperidone lactams 1 – 14 were converted to linear‐chain enantiopure amino diols 15 – 26 by reduction with LiNH 2 BH 3 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.