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Synthesis of All the Diastereomers of 2‐Amino‐3‐hydroxy‐4,5‐dimethylhexanoic Acid
Author(s) -
Spengler Jan,
Albericio Fernando
Publication year - 2014
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.201301257
Subject(s) - diastereomer , chemistry , stereoselectivity , aldehyde , olefin fiber , yield (engineering) , intramolecular force , hydrolysis , catalysis , stereochemistry , organic chemistry , materials science , metallurgy
Herein, we describe an efficient stereoselective synthesis of all the diastereomers of 2‐amino‐3‐hydroxy‐4,5‐dimethylhexanoic acid. The γ‐branched carbon skeleton was set up by reaction of Garner's aldehyde with 2‐lithio‐3‐methyl‐2‐butene. Hydrogenation (Pd/C catalyst) of the tetrasubstituted olefin proceeded smoothly with acceptable stereoselectivity, depending on the diastereomer hydrogenated. The final compounds were then obtained in 12–18 % overall yield through intramolecular cyclization, Jones oxidation, and hydrolysis in 5–7 steps from Garner's aldehyde.