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At elevated temperature (refluxing THF) prenyl anion adds regio- and enantioselectively to aldehyde 1 when a chiral, borneol-derived ligand is present. This reaction is the key stepin the first total synthesis of the monoterpene (−)-rosiridol (retrosynthesis is shown on the right). In addition, the absolute configuration of this natural product has been assigned conclusively. M=Zn, R=tBuMe2Si.
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Hong et al. (1998) studied this question.
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