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Intramolecular Diels–Alder reactions using chiral ruthenium Lewis acids and application in the total synthesis of ent-ledol

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Published in Organic and Biomolecular Chemistry. 2011, vol. 9, no. 21, p. 7564-7570
Abstract One-point binding chiral ruthenium Lewis acids incorporating the C2-symmetric electron-poor bidentate phosphinite ligand BIPHOP-F and a Cp or an indenyl ‘roof’ can efficiently catalyze asymmetric intramolecular Diels–Alder reactions of trienes to form bicyclic adducts with good to excellent asymmetric induction. This reaction forms the key step in a total synthesis of ent-ledol in 96% ee. The synthesis also helps to clarify the stereochemical assignment of ledol and inconsistencies in the measured optical rotation.
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Other version: http://xlink.rsc.org/?DOI=c1ob06121f
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THAMAPIPOL, Sirinporn, KUNDIG, Ernst Peter. Intramolecular Diels–Alder reactions using chiral ruthenium Lewis acids and application in the total synthesis of ent-ledol. In: Organic and Biomolecular Chemistry, 2011, vol. 9, n° 21, p. 7564-7570. https://archive-ouverte.unige.ch/unige:17738

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Deposited on : 2011-12-06

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