Sharpless epoxidation of (E)‐1‐(trimethylsilyl)[1‐2H1]oct‐1‐en‐3‐o1 (3a) yielded (1S,2S,3S)‐ and (1R,2R,3R)‐1‐(trimethylsilyl)‐1,2‐epoxy[1‐2H1]octan‐3‐ols (4a and 4b, resp.) which were converted in three steps into (S)‐ and (R)‐fluoro[ 2H1]acetic acid (7a and 7b, resp.) in good yields. Their high isotopic and optical purity was established by 1H‐ and 19F‐NMR, mass, and circular‐dichroism spectroscopy.
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Gartz et al. (1996) studied this question.
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