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Stereoselective Synthesis of (2 R ,5 R )‐ and (2 S ,5 R )‐5‐Hydroxylysine
Author(s) -
van den Nieuwendijk Adrianus M. C. H.,
Kriek Nicole M. A. J.,
Brussee Johannes,
van Boom Jacques H.,
van der Gen Arne
Publication year - 2000
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 - 10.1002/1099-0690(200011)2000:22<3683::aid-ejoc3683>3.0.co;2-u
Subject(s) - hydroxylysine , chemistry , stereoselectivity , stereochemistry , chirality (physics) , glycine , axial chirality , enantioselective synthesis , amino acid , catalysis , organic chemistry , biochemistry , lysine , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
A stereoselective synthesis of (2 S ,5 R )‐5‐hydroxylysine ( 1 ) and (2 R ,5 R )‐5‐hydroxylysine ( 17 ), based on a concept involving Williams glycine template methodology and ( R )‐hydroxynitrile lyase for the introduction of chirality at the α‐position and the side‐chain, respectively, is described. This strategy offers an expeditious route towards orthogonally protected 5‐hydroxylysines.