Stereodivergent organocatalytic intramolecular michael addition/ lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans

Dorine Belmessieri; Alix De La Houpliere; Ewen D.D. Calder; James E. Taylor; Andrew D. Smith

doi:10.1002/chem.201402684

Stereodivergent organocatalytic intramolecular michael addition/ lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans

Dorine Belmessieri, Alix De La Houpliere, Ewen D.D. Calder, James E. Taylor, Andrew D. Smith

Department of Chemistry

University of St Andrews

Research output: Contribution to journal › Article › peer-review

51 Citations (SciVal)

Abstract

A stereodivergent asymmetric Lewis base catalyzed Michael addition/lactonization of enone acids into substituted dihydrobenzofuran and tetrahydrofuran derivatives is reported. Commercially available (S)-(-)-tetramisole hydrochloride gives products with high syn diastereoselectivity in excellent enantioselectivity (up to 99:1 d.r. _syn/anti, 99% ee_syn), whereas using a cinchona alkaloid derived catalyst gives the corresponding anti-diastereoisomers as the major product (up to 10:90 d.r._syn/anti, 99% ee_anti). You can have it both ways! A stereodivergent asymmetric Lewis base catalyzed Michael addition/lactonization of enone acids into substituted dihydrobenzofuran and tetrahydrofuran derivatives is reported, giving products with high d.r. and ee (see scheme).

Original language	English
Pages (from-to)	9762-9769
Number of pages	8
Journal	Chemistry - A European Journal
Volume	20
Issue number	31
Early online date	2 Jul 2014
DOIs	https://doi.org/10.1002/chem.201402684
Publication status	Published - 28 Jul 2014

Keywords

asymmetric catalysis
cinchona alkaloid
isothiourea
Michael addition
organocatalysis
oxygen heterocycles
stereodivergent

ASJC Scopus subject areas

General Chemistry

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Stereodivergent organocatalytic intramolecular michael addition/ lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans. / Belmessieri, Dorine; De La Houpliere, Alix; Calder, Ewen D.D. et al.
In: Chemistry - A European Journal, Vol. 20, No. 31, 28.07.2014, p. 9762-9769.

Research output: Contribution to journal › Article › peer-review

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AU - De La Houpliere, Alix

AU - Calder, Ewen D.D.

AU - Taylor, James E.

AU - Smith, Andrew D.

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Stereodivergent organocatalytic intramolecular michael addition/ lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans

Abstract

Keywords

ASJC Scopus subject areas

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