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Chiral Tricarbonyl(η6-cyclobutabenzene)chromium Complexes. Diastereoselective Synthesis and Use in Asymmetric Cycloaddition Reactions

Authors
Leresche, James
Published in Tetrahedron. 1996, vol. 52, no. 21, p. 7363-7378
Abstract The intermolecular Diels-Alder reaction of a nonracemic planar chiral (ortho-quinodimethane)Cr(CO)3 intermediate 6 with dienophiles gave, after decomplexation, chiral nonracemic tetralins 23–25. Access to 6 was obtained via enzyme catalyzed acetate hydrolysis of 1-acetoxycyclobutabenzene (13), derivatization of the highly enantioenriched 1-hydroxycyclobutabenzene (S-(+)-8) as the tetrahydropyranyl ether 20 diastereoselective complexation to Cr(CO)3 followed by hydrolysis and charge accelerated electrocyclic ring opening of the anion of (1-hydroxycyclobutabenzene)Cr(CO)3 ((1S,6aR)-(-)-4).
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KUNDIG, Ernst Peter et al. Chiral Tricarbonyl(η6-cyclobutabenzene)chromium Complexes. Diastereoselective Synthesis and Use in Asymmetric Cycloaddition Reactions. In: Tetrahedron, 1996, vol. 52, n° 21, p. 7363-7378. https://archive-ouverte.unige.ch/unige:6969

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Deposited on : 2010-06-18

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