Asymmetric Organocatalysis Revisited: Taming Hydrindanes with Jørgensen–Hayashi Catalyst

Yannick Stöckl; Wolfgang Frey; Johannes Lang; Birgit Claasen; Angelika Baro; Sabine Laschat

doi:10.1055/s-0037-1610409

Synthesis, Table of Contents

CC BY ND NC 4.0 · Synthesis 2019; 51(05): 1123-1134
DOI: 10.1055/s-0037-1610409

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Asymmetric Organocatalysis Revisited: Taming Hydrindanes with Jørgensen–Hayashi Catalyst

Yannick Stöckl

,

Wolfgang Frey

,

Johannes Lang

,

Birgit Claasen

,

Angelika Baro

,

Sabine Laschat *

Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany Email: sabine.laschat@oc.uni-stuttgart.de

› Author Affiliations

Abstract

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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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