Asymmetric Organocatalysis Revisited: Taming Hydrindanes with Jørgensen–Hayashi Catalyst

Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

The organocatalytic Michael reaction of easily available 1-cyclopentene-1-carbaldehyde and 1,3-dicarbonyl compounds led to cyclopentanecarbaldehydes on a gram scale with low catalyst loading (2 mol%) and high enantioselectivity. The synthetic potential of 4-acylhexahydroindenones from intramolecular aldol condensation was demonstrated by Diels–Alder reaction to a tetracyclic derivative with seven stereogenic centers. The diastereofacial preference of the tetracyclic product was confirmed by DFT calculations. The described reaction sequence is characterized by few redox-economic steps and high degree of molecular complexity.

Key words

organocatalysis - hydrindane - Jørgensen–Hayashi catalyst - Michael addition - aldol condensation - Diels–Alder reaction

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