Enantioselective Diels–Alder reactions with anomalous endo/exo selectivities using conformationally flexible chiral supramolecular catalysts

…, T Mizuno, A Izumiseki, R Usami, T Asai…

Index: Hatano, Manabu; Mizuno, Tomokazu; Izumiseki, Atsuto; Usami, Ryota; Asai, Takafumi; Akakura, Matsujiro; Ishihara, Kazuaki Angewandte Chemie - International Edition, 2011 , vol. 50, # 51 p. 12189 - 12192

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Citation Number: 31

Abstract

On the basis of Woodward–Hoffmann frontier molecular orbital interactions and steric interactions between dienes and dienophiles during the formation of [2+ 4] pericyclic transition states, endo/exo selectivity in the Diels–Alder reaction strongly depends on the substrates.[1] Therefore, it is quite difficult to control both enantioselectivity [2] and anomalous endo/exo selectivity by conventional chiral catalysts, which can discriminate ...