Chiral Brønsted acid catalyzed stereoselective addition of azlactones to 3-vinylindoles for facile access to enantioenriched tryptophan derivatives

Masahiro Terada; Kenichi Moriya; Kyohei Kanomata; Keiichi Sorimachi

doi:10.1002/anie.201105562

Chiral Brønsted acid catalyzed stereoselective addition of azlactones to 3-vinylindoles for facile access to enantioenriched tryptophan derivatives

Masahiro Terada, Kenichi Moriya, Kyohei Kanomata, Keiichi Sorimachi

SCI - Chemistry

Tohoku University

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

77 Citations (Scopus)

Abstract

Syn-gled out: The syn diastereo- and enantioselective addition of azlactones to 3-vinylindoles was accomplished by using a chiral, binapthol-derived, Brønsted acid catalyst (see scheme). This method enables facile access to tryptophan derivatives with adjacent quaternary and tertiary stereogenic centers, which are potentially useful for the synthesis of peptidomimetics.

Original language	English
Pages (from-to)	12586-12590
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	52
DOIs	https://doi.org/10.1002/anie.201105562
Publication status	Published - 2011 Dec 23

Keywords

asymmetric catalysis
azlactones
indoles
organocatalysis
tryptophan

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10.1002/anie.201105562

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abstract = "Syn-gled out: The syn diastereo- and enantioselective addition of azlactones to 3-vinylindoles was accomplished by using a chiral, binapthol-derived, Br{\o}nsted acid catalyst (see scheme). This method enables facile access to tryptophan derivatives with adjacent quaternary and tertiary stereogenic centers, which are potentially useful for the synthesis of peptidomimetics.",

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Chiral Brønsted acid catalyzed stereoselective addition of azlactones to 3-vinylindoles for facile access to enantioenriched tryptophan derivatives. / Terada, Masahiro; Moriya, Kenichi; Kanomata, Kyohei et al.
In: Angewandte Chemie - International Edition, Vol. 50, No. 52, 23.12.2011, p. 12586-12590.

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

TY - JOUR

T1 - Chiral Brønsted acid catalyzed stereoselective addition of azlactones to 3-vinylindoles for facile access to enantioenriched tryptophan derivatives

AU - Terada, Masahiro

AU - Moriya, Kenichi

AU - Kanomata, Kyohei

AU - Sorimachi, Keiichi

PY - 2011/12/23

Y1 - 2011/12/23

N2 - Syn-gled out: The syn diastereo- and enantioselective addition of azlactones to 3-vinylindoles was accomplished by using a chiral, binapthol-derived, Brønsted acid catalyst (see scheme). This method enables facile access to tryptophan derivatives with adjacent quaternary and tertiary stereogenic centers, which are potentially useful for the synthesis of peptidomimetics.

AB - Syn-gled out: The syn diastereo- and enantioselective addition of azlactones to 3-vinylindoles was accomplished by using a chiral, binapthol-derived, Brønsted acid catalyst (see scheme). This method enables facile access to tryptophan derivatives with adjacent quaternary and tertiary stereogenic centers, which are potentially useful for the synthesis of peptidomimetics.

KW - asymmetric catalysis

KW - azlactones

KW - indoles

KW - organocatalysis

KW - tryptophan

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JF - Angewandte Chemie - International Edition

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Chiral Brønsted acid catalyzed stereoselective addition of azlactones to 3-vinylindoles for facile access to enantioenriched tryptophan derivatives

Abstract

Keywords

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