Chemical communications

An enantioselective desymmetrisation approach to C9-substituted trans-hydrindene rings based on a diastereotopic group-selective intramolecular Diels–Alder …

N Azzi, E Griffen, M Light, B Linclau

Index: Azzi, Nadia; Griffen, Ed; Light, Mark; Linclau, Bruno Chemical Communications, 2006 , # 47 p. 4909 - 4911

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Citation Number: 3

Abstract

The formation of a hydrindene ring system via an intramolecular Diels–Alder reaction (IMDA) has been extensively studied. 1 The reaction with (E,E,E)-substrates usually affords a trans-fused hydrindene ring resulting from an endo-transition state. Several Lewis acids and organocatalysts have been shown to induce excellent enantioselectivity for the IMDA reaction towards hydrindene rings. 2 In addition, a range of chiral auxiliaries proved very efficient for inducing facial ...