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Title
| - Diastereoselective Ring-Closing Metathesis in the Synthesis ofDihydropyrans
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Abstract
| - An investigation into the factors influencing the diastereochemical outcome of the ring-closingmetathesis based synthesis of dihydropyrans is presented in this paper. Divinyl carbinols derivedfrom α-hydroxy carboxylic acid esters are elaborated to trienes with two diastereotopic vinyl moieties.Depending on the steric demand of the oxo substituent of the divinyl carbinol moiety (eitherunprotected OH, TBDMS, or benzyl ether) different diastereomers are preferrably formed uponring-closing metathesis. An extension to diastereoselective double ring-closing metathesis in theformation of spirocycles has also been investigated.
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