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

D. Belmessieri; A. De La Houpliere; E.D.D. Calder; J.E. Taylor; A.D. Smith

doi:10.1002/chem.201402684

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

D. Belmessieri
, A. De La Houpliere
, E.D.D. Calder
, J.E. Taylor
, A.D. Smith

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

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. , 99% ee), whereas using a cinchona alkaloid derived catalyst gives the corresponding anti-diastereoisomers as the major product (up to 10:90 d.r., 99% ee). 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
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

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10.1002/chem.201402684

Smith_2015_ChemEU_Stereo_CC
© 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/), which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
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Applications of isothioureas in organocatalysis: kinetic resolution of secondary alcohols and intramolecular Michael addition-lactonisation
Belmessieri, D. (Author), Smith, A. (Supervisor), 25 Jun 2014
Student thesis: Doctoral Thesis (PhD)
Title redacted
De La Houpliere, A. (Author), Smith, A. (Supervisor), 21 Jun 2017
Student thesis: Doctoral Thesis (PhD)

Cite this

@article{d434bd90639b43cabe8434a619f7448b,

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

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. , 99\% ee), whereas using a cinchona alkaloid derived catalyst gives the corresponding anti-diastereoisomers as the major product (up to 10:90 d.r., 99\% ee). 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).",

keywords = "Asymmetric catalysis, Cinchona alkaloid, Isothiourea, Michael addition, Organocatalysis, Oxygen heterocycles, Stereodivergent",

author = "D. Belmessieri and \{De La Houpliere\}, A. and E.D.D. Calder and J.E. Taylor and A.D. Smith",

note = "The authors thank the Royal Society for a University Research Fellowship (A.D.S.), the European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007–2013), ERC Grant Agreement No. 279850 (A.D.L.H. and J.E.T.), and the EPSRC (DTA studentship to D.B.) for funding.",

year = "2014",

month = jul,

day = "28",

doi = "10.1002/chem.201402684",

language = "English",

volume = "20",

pages = "9762--9769",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley \& Sons, Ltd",

number = "31",

}

Stereodivergent organocatalytic intramolecular michael addition/ lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans. / Belmessieri, D.; De La Houpliere, A.; Calder, E.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

TY - JOUR

T1 - Stereodivergent organocatalytic intramolecular michael addition/ lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans

AU - Belmessieri, D.

AU - De La Houpliere, A.

AU - Calder, E.D.D.

AU - Taylor, J.E.

AU - Smith, A.D.

N1 - The authors thank the Royal Society for a University Research Fellowship (A.D.S.), the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013), ERC Grant Agreement No. 279850 (A.D.L.H. and J.E.T.), and the EPSRC (DTA studentship to D.B.) for funding.

PY - 2014/7/28

Y1 - 2014/7/28

N2 - 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. , 99% ee), whereas using a cinchona alkaloid derived catalyst gives the corresponding anti-diastereoisomers as the major product (up to 10:90 d.r., 99% ee). 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).

AB - 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. , 99% ee), whereas using a cinchona alkaloid derived catalyst gives the corresponding anti-diastereoisomers as the major product (up to 10:90 d.r., 99% ee). 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).

KW - Asymmetric catalysis

KW - Cinchona alkaloid

KW - Isothiourea

KW - Michael addition

KW - Organocatalysis

KW - Oxygen heterocycles

KW - Stereodivergent

U2 - 10.1002/chem.201402684

DO - 10.1002/chem.201402684

M3 - Article

AN - SCOPUS:84905659539

SN - 0947-6539

VL - 20

SP - 9762

EP - 9769

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 31

ER -

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

Abstract

Keywords

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Student theses

Applications of isothioureas in organocatalysis: kinetic resolution of secondary alcohols and intramolecular Michael addition-lactonisation

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Cite this