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Alkenyloxazolines such as 7 undergo double addition of isocyanates as shown in Scheme 1. In contrast, the corresponding thiazolines only give single addition, although a further equivalent of isocyanate can be added under more forcing conditions. The reaction with a chloroformate would be directly analogous to this: M. C. Elliott, A. E. Monk, E. Kruiswijk, D. E. Hibbs, R. L. Jenkins and D. V. Jones, Synlett., 1999, 1379.
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3843151839
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note
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A more direct route would involve Eschenmoser sulfide contraction with ethyl 2-bromoacetate. However, we found this to be low-yielding and capricious, such that the present route was the most efficient.
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