Enantioselective organocatalyzed Oxa-Michael-Aldol cascade reactions: Construction of chiral 4H-chromenes with a trifluoromethylated tetrasubstituted carbon stereocenter

Jing Zhang; Manjaly John Ajitha; Lin He; Kai Liu; Bin Dai; Kuo-Wei Huang

doi:10.1002/adsc.201400977

Enantioselective organocatalyzed Oxa-Michael-Aldol cascade reactions: Construction of chiral 4H-chromenes with a trifluoromethylated tetrasubstituted carbon stereocenter

Jing Zhang, Manjaly John Ajitha, Lin He, Kai Liu, Bin Dai, Kuo-Wei Huang

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

20 Scopus citations

Abstract

The first organocatalytic asymmetric synthesis of 4H-chromenes bearing a trifluoromethylated tetrasubstituted carbon center is presented. Chiral secondary amines promote the oxa-Michael-aldol cascade reaction between alkynals and 2-trifluoroacetylphenols via iminium-allenamine activation to produce pharmaceutically important heterocycles with excellent enantioselectivities. The proposed reaction can be scaled-up easily with maintenance of the excellent enantioselectivity. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Original language	English (US)
Pages (from-to)	967-973
Number of pages	7
Journal	Advanced Synthesis & Catalysis
Volume	357
Issue number	5
DOIs	https://doi.org/10.1002/adsc.201400977
State	Published - Mar 13 2015

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: This work was supported by the National Natural Science Foundation of China (Nos. 21162022, 21428302) and Shihezi University (Nos. 2011ZRKXTD04, 2012ZRKXJQ06).

ASJC Scopus subject areas

Organic Chemistry
Catalysis

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10.1002/adsc.201400977

Cite this

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title = "Enantioselective organocatalyzed Oxa-Michael-Aldol cascade reactions: Construction of chiral 4H-chromenes with a trifluoromethylated tetrasubstituted carbon stereocenter",

abstract = "The first organocatalytic asymmetric synthesis of 4H-chromenes bearing a trifluoromethylated tetrasubstituted carbon center is presented. Chiral secondary amines promote the oxa-Michael-aldol cascade reaction between alkynals and 2-trifluoroacetylphenols via iminium-allenamine activation to produce pharmaceutically important heterocycles with excellent enantioselectivities. The proposed reaction can be scaled-up easily with maintenance of the excellent enantioselectivity. {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

author = "Jing Zhang and Ajitha, {Manjaly John} and Lin He and Kai Liu and Bin Dai and Kuo-Wei Huang",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported by the National Natural Science Foundation of China (Nos. 21162022, 21428302) and Shihezi University (Nos. 2011ZRKXTD04, 2012ZRKXJQ06).",

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T1 - Enantioselective organocatalyzed Oxa-Michael-Aldol cascade reactions: Construction of chiral 4H-chromenes with a trifluoromethylated tetrasubstituted carbon stereocenter

AU - Zhang, Jing

AU - Ajitha, Manjaly John

AU - He, Lin

AU - Liu, Kai

AU - Dai, Bin

AU - Huang, Kuo-Wei

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported by the National Natural Science Foundation of China (Nos. 21162022, 21428302) and Shihezi University (Nos. 2011ZRKXTD04, 2012ZRKXJQ06).

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Y1 - 2015/3/13

N2 - The first organocatalytic asymmetric synthesis of 4H-chromenes bearing a trifluoromethylated tetrasubstituted carbon center is presented. Chiral secondary amines promote the oxa-Michael-aldol cascade reaction between alkynals and 2-trifluoroacetylphenols via iminium-allenamine activation to produce pharmaceutically important heterocycles with excellent enantioselectivities. The proposed reaction can be scaled-up easily with maintenance of the excellent enantioselectivity. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - The first organocatalytic asymmetric synthesis of 4H-chromenes bearing a trifluoromethylated tetrasubstituted carbon center is presented. Chiral secondary amines promote the oxa-Michael-aldol cascade reaction between alkynals and 2-trifluoroacetylphenols via iminium-allenamine activation to produce pharmaceutically important heterocycles with excellent enantioselectivities. The proposed reaction can be scaled-up easily with maintenance of the excellent enantioselectivity. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Enantioselective organocatalyzed Oxa-Michael-Aldol cascade reactions: Construction of chiral 4H-chromenes with a trifluoromethylated tetrasubstituted carbon stereocenter

Abstract

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ASJC Scopus subject areas

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Other files and links

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CCDC 1027232: Experimental Crystal Structure Determination : 4-hydroxy-2-(2-naphthyl)-4-(trifluoromethyl)-4H-chromene-3-carbaldehyde

Cite this

Enantioselective organocatalyzed Oxa-Michael-Aldol cascade reactions: Construction of chiral 4H-chromenes with a trifluoromethylated tetrasubstituted carbon stereocenter

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1027232: Experimental Crystal Structure Determination : 4-hydroxy-2-(2-naphthyl)-4-(trifluoromethyl)-4H-chromene-3-carbaldehyde

Cite this