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

Published inOrganic & biomolecular chemistry, vol. 9, no. 21, p. 7564-7570
Publication date2011
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.

Citation (ISO format)
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 & biomolecular chemistry, 2011, vol. 9, n° 21, p. 7564–7570. doi: 10.1039/c1ob06121f
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ISSN of the journal1477-0520
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Creation12/05/2011 2:42:00 PM
First validation12/05/2011 2:42:00 PM
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