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A Practical Synthesis of Enantiopure ( R )‐4‐Hydroxy‐2‐cyclohexen‐1‐one
Author(s) -
Gebauer Olaf,
Brückner Reinhard
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619961010
Subject(s) - enantiopure drug , chemistry , stereoselectivity , enantiomer , vicinal , quinic acid , yield (engineering) , alcohol , ether , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , materials science , metallurgy
The title compound R ‐ 4a was prepared from (–)‐quinic acid ( 1 ) in 6 steps in 18% overall yield (Scheme 3) and with 100% enantiomeric purity (Figure 1). The initiating step is the regio‐ and stereoselective acetalization of the trans ‐oriented vicinal OH groups of 1 (+ 5 → 8 ). Alcohol R ‐ 4a can be protected as the 2‐ethoxyethyl ether R ‐ 4e (78%).
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