Asymmetric synthesis of functionalized tetrahydrofluorenones via an NHC-catalyzed homoenolate Michael addition

Tao Shu; Sun Li; Xiang-Yu Chen; Qiang Liu; Carolina von Essen; Kari Rissanen; Dieter Enders

doi:10.1039/C8CC04145H

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Asymmetric synthesis of functionalized tetrahydrofluorenones via an NHC-catalyzed homoenolate Michael addition†

Tao Shu,^a Sun Li,^a Xiang-Yu Chen,^a Qiang Liu,^a Carolina von Essen,^b Kari Rissanen

^b and Dieter Enders

*^a

Author affiliations

* Corresponding authors

^a Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
E-mail: enders@rwth-aachen.de

^b Department of Chemistry, University of Jyväskylä, P.O. Box 35, 40014 Jyväskylä, Finland

Abstract

The first example of an N-heterocyclic carbene-catalyzed asymmetric desymmetrization of enal-tethered cyclohexadienones via an intramolecular homoenolate Michael addition/esterification reaction is described. This new protocol offers a direct entry to various functionalized tetrahydrofluorenones with three contiguous stereocenters in high yields, good diastereoselectivities and excellent enantioselectivities.

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DOI: https://doi.org/10.1039/C8CC04145H
Article type: Communication
Submitted: 24 May 2018
Accepted: 14 Jun 2018
First published: 15 Jun 2018

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Chem. Commun., 2018,54, 7661-7664

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Asymmetric synthesis of functionalized tetrahydrofluorenones via an NHC-catalyzed homoenolate Michael addition

T. Shu, S. Li, X. Chen, Q. Liu, C. von Essen, K. Rissanen and D. Enders, Chem. Commun., 2018, 54, 7661 DOI: 10.1039/C8CC04145H

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Chemical Communications

Asymmetric synthesis of functionalized tetrahydrofluorenones via an NHC-catalyzed homoenolate Michael addition†

Abstract

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Asymmetric synthesis of functionalized tetrahydrofluorenones via an NHC-catalyzed homoenolate Michael addition

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