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Synthesis and Circular Dichroism of Both Enantiomers of 2‐deuterofluoroacetic acid ( Fluoro[ 2 H 1 ]acetic acid)
Author(s) -
Gartz Dagmar,
Reed Jennifer,
Rétey János
Publication year - 1996
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19960790411
Subject(s) - chemistry , acetic acid , circular dichroism , trimethylsilyl , enantiomer , enantiomeric excess , spectroscopy , stereochemistry , nuclear magnetic resonance spectroscopy , medicinal chemistry , organic chemistry , enantioselective synthesis , catalysis , physics , quantum mechanics
Sharpless epoxidation of ( E )‐1‐(trimethylsilyl)[1‐ 2 H 1 ]oct‐1‐en‐3‐o1 ( 3a ) yielded (1 S ,2 S ,3 S )‐ and (1 R ,2 R ,3 R )‐1‐(trimethylsilyl)‐1,2‐epoxy[1‐ 2 H 1 ]octan‐3‐ols ( 4a and 4b , resp.) which were converted in three steps into ( S )‐ and ( R )‐fluoro[ 2 H 1 ]acetic acid ( 7a and 7b , resp.) in good yields. Their high isotopic and optical purity was established by 1 H‐ and 19 F‐NMR, mass, and circular‐dichroism spectroscopy.
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