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Generation of and cycloaddition to an enantiomerically pure α-oxy-ortho-quinodimethane-tricarbonylchromium complex intermediate

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Leresche, J.
Published in Journal of the Chemical Society. Chemical Communications. 1991, no. 24, p. 1713-1715
Abstract The reaction of BunLi with either syn- or anti-n6-(1-acetoxycyclobutabenzene)Cr(CO)3 generates under mild conditions the planar chiral ortho-quinodimethane complex intermediate 4 which reacts with dienophiles (methyl acrylate, acrylonitrile, dimethyl fumarate) highly stereoselectively from the face opposite the metal to give the anti-1-hydroxytetrahydronaphthalene–Cr(CO)3 complexes (X-ray structures of 5 and 6) and, after decomplexation, the 1-hydroxytetrahydronaphthalenes 7–14(asymmetric synthesis of 7 and 8).
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KUNDIG, Ernst Peter, BERNARDINELLI, Gérald Hugues, LERESCHE, J. Generation of and cycloaddition to an enantiomerically pure α-oxy-ortho-quinodimethane-tricarbonylchromium complex intermediate. In: Journal of the Chemical Society. Chemical Communications, 1991, n° 24, p. 1713-1715. https://archive-ouverte.unige.ch/unige:7799

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Deposited on : 2010-06-21

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