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Synthesis of Racemic δ,δ‐Dimethylproline Derivatives
Author(s) -
Rodríguez Isabel,
Calaza M. Isabel,
Cativiela Carlos
Publication year - 2013
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.201201420
Subject(s) - chemistry , trifluoromethanesulfonate , yield (engineering) , stereoselectivity , organic chemistry , phenylboronic acid , amino acid , derivative (finance) , combinatorial chemistry , catalysis , biochemistry , materials science , economics , financial economics , metallurgy
A versatile methodology for the preparation of racemic δ,δ‐dimethylproline derivatives has been developed. Methyl N ‐Boc‐δ,δ‐dimethylprolinate was synthesized from a β‐amino acid in six steps and 55 % overall yield. The route is amenable to the preparation of a broad range of δ,δ‐disubstituted prolines by starting with the adequate β‐amino acids. In addition, one of the intermediate compounds in the synthetic route has been used for the preparation of a δ,δ‐dimethylproline derivative that is substituted at the β‐position with a phenyl group. This has been achieved by coupling phenylboronic acid with a regioselectively generated vinyl triflate followed by a stereoselective hydrogenation.