The direct asymmetric vinylogous aldol reaction of furanones with α-ketoesters: Access to chiral γ-Butenolides and glycerol derivatives

Jie Luo; Haifei Wang; Xiao Han; Liwen Xu; Jacek Kwiatkowski; Kuo-Wei Huang; Yixin Lu

doi:10.1002/anie.201006316

The direct asymmetric vinylogous aldol reaction of furanones with α-ketoesters: Access to chiral γ-Butenolides and glycerol derivatives

Jie Luo, Haifei Wang, Xiao Han, Liwen Xu, Jacek Kwiatkowski, Kuo-Wei Huang, Yixin Lu

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

117 Scopus citations

Abstract

Twice as good: The title reaction using the tryptophan-derived bifunctional organic catalyst 1 has been developed. The reported method led to the synthesis of chiral γ-substituted butenolides in excellent yields, with high diastereo- and enantioselectivities. Facile synthesis of chiral glycerol derivatives containing a tertiary hydroxy group has also been demonstrated. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Original language	English (US)
Pages (from-to)	1861-1864
Number of pages	4
Journal	Angewandte Chemie International Edition
Volume	50
Issue number	8
DOIs	https://doi.org/10.1002/anie.201006316
State	Published - Jan 11 2011

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: We thank the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112) for generous financial support.

ASJC Scopus subject areas

Chemistry(all)
Catalysis

Access to Document

10.1002/anie.201006316

Cite this

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title = "The direct asymmetric vinylogous aldol reaction of furanones with α-ketoesters: Access to chiral γ-Butenolides and glycerol derivatives",

abstract = "Twice as good: The title reaction using the tryptophan-derived bifunctional organic catalyst 1 has been developed. The reported method led to the synthesis of chiral γ-substituted butenolides in excellent yields, with high diastereo- and enantioselectivities. Facile synthesis of chiral glycerol derivatives containing a tertiary hydroxy group has also been demonstrated. {\textcopyright} 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

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T1 - The direct asymmetric vinylogous aldol reaction of furanones with α-ketoesters: Access to chiral γ-Butenolides and glycerol derivatives

AU - Luo, Jie

AU - Wang, Haifei

AU - Han, Xiao

AU - Xu, Liwen

AU - Kwiatkowski, Jacek

AU - Huang, Kuo-Wei

AU - Lu, Yixin

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We thank the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112) for generous financial support.

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N2 - Twice as good: The title reaction using the tryptophan-derived bifunctional organic catalyst 1 has been developed. The reported method led to the synthesis of chiral γ-substituted butenolides in excellent yields, with high diastereo- and enantioselectivities. Facile synthesis of chiral glycerol derivatives containing a tertiary hydroxy group has also been demonstrated. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - Twice as good: The title reaction using the tryptophan-derived bifunctional organic catalyst 1 has been developed. The reported method led to the synthesis of chiral γ-substituted butenolides in excellent yields, with high diastereo- and enantioselectivities. Facile synthesis of chiral glycerol derivatives containing a tertiary hydroxy group has also been demonstrated. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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The direct asymmetric vinylogous aldol reaction of furanones with α-ketoesters: Access to chiral γ-Butenolides and glycerol derivatives

Abstract

Bibliographical note

ASJC Scopus subject areas

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Other files and links

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CCDC 803555: Experimental Crystal Structure Determination : (S,S)-t-Butyl (3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)(hydroxy)2-naphthylacetate

Cite this

The direct asymmetric vinylogous aldol reaction of furanones with α-ketoesters: Access to chiral γ-Butenolides and glycerol derivatives

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 803555: Experimental Crystal Structure Determination : (S,S)-t-Butyl (3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)(hydroxy)2-naphthylacetate

Cite this