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the (, R,)-methoxy butenolide, 4, and the chiral radical, as the coupling of the, S, enantiomer of, 4, with the radical generated from, 5 a, gave a 4.01 ratio of the products of, anti, and, syn, addition. The nature of the butenolide radical acceptor and the 40 °C difference in reaction temperature must be responsible for the lower stereoselectivity that we observe compared to that reported by Barton. Our experiments were conducted with the (, R,)-butenolide, 4, because this enantiomer was required for the synthesis of (−)-chromodorolide B.
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The Boltzmann distribution is exponentialsmall energetic errors accumulate 1 kcal mol, error changes the selectivity from 2.31 to 12.3 (±0.5 kcal mol
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−1).
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