Syntheses of α-CF3-α-quaternary ketones via p-quinone methides and their derivatization to compounds with successively congested stereogenic centers

Kyu Terashima; Tomoko Kawasaki-Takasuka; Tomohiro Agou; Toshio Kubota; Takashi Yamazaki

doi:10.1039/d0ob00951b

Syntheses of α-CF3-α-quaternary ketones via p-quinone methides and their derivatization to compounds with successively congested stereogenic centers

Organic & Biomolecular Chemistry ◽

10.1039/d0ob00951b ◽

2020 ◽

Vol 18 (24) ◽

pp. 4638-4644 ◽

Cited By ~ 1

Author(s):

Kyu Terashima ◽

Tomoko Kawasaki-Takasuka ◽

Tomohiro Agou ◽

Toshio Kubota ◽

Takashi Yamazaki

Keyword(s):

Quinone Methides ◽

Conjugate Additions ◽

Stereogenic Centers

NHC-catalyzed 1,6-conjugate additions of a variety of aldehydes to δ-CF3-δ-substituted p-quinone methides and their highly diastereoselective derivatization to compounds with successively congested stereogenic centers were performed.

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Non-hydrogen bond catalyst-mediated diastereoselective conjugate additions of 5H-oxazol-4-ones to o-hydroxyphenyl-substituted p-quinone methides

Organic & Biomolecular Chemistry ◽

10.1039/d0ob01558j ◽

2020 ◽

Vol 18 (35) ◽

pp. 6807-6811

Author(s):

Ziyang Wang ◽

Anqi Huang ◽

Fang Fang ◽

Pengfei Li ◽

Guokai Liu ◽

...

Keyword(s):

Hydrogen Bond ◽

Conjugate Addition ◽

Quinone Methides ◽

Conjugate Additions ◽

High Yields

An efficient DBU-catalyzed conjugate addition of 5H-oxazol-4-ones to o-hydroxyphenyl-substituted p-quinone methides has been developed, affording the valuable diarylmethanes in high yields with excellent diastereoselectivity.

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Enantioselective Synthesis of Quaternary Carbon Stereogenic Centers through Copper-Catalyzed Conjugate Additions of Aryl- and Alkylaluminum Reagents to Acyclic Trisubstituted Enones

Angewandte Chemie International Edition ◽

10.1002/anie.201304035 ◽

2013 ◽

Vol 52 (31) ◽

pp. 8156-8159 ◽

Cited By ~ 46

Author(s):

Jennifer A. Dabrowski ◽

Matthew T. Villaume ◽

Amir H. Hoveyda

Keyword(s):

Enantioselective Synthesis ◽

Quaternary Carbon ◽

Conjugate Additions ◽

Stereogenic Centers

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All-Carbon Quaternary Stereogenic Centers by Enantioselective Cu-Catalyzed Conjugate Additions Promoted by a Chiral N-Heterocyclic Carbene.

ChemInform ◽

10.1002/chin.200723057 ◽

2007 ◽

Vol 38 (23) ◽

Author(s):

M. Kevin Brown ◽

Tricia L. May ◽

Carl A. Baxter ◽

Amir H. Hoveyda

Keyword(s):

Conjugate Additions ◽

Stereogenic Centers ◽

Quaternary Stereogenic Centers

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Enantioselective Synthesis of All-Carbon Quaternary Stereogenic Centers by Catalytic Asymmetric Conjugate Additions of Alkyl and Aryl Aluminum Reagents to Five-, Six-, and Seven-Membered-Ring β-Substituted Cyclic Enones

Angewandte Chemie International Edition ◽

10.1002/anie.200802910 ◽

2008 ◽

Vol 47 (38) ◽

pp. 7358-7362 ◽

Cited By ~ 151

Author(s):

Tricia L. May ◽

M. Kevin Brown ◽

Amir H. Hoveyda

Keyword(s):

Membered Ring ◽

Enantioselective Synthesis ◽

Conjugate Additions ◽

Stereogenic Centers ◽

Cyclic Enones ◽

Catalytic Asymmetric ◽

Quaternary Stereogenic Centers

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Formation of Vinyl-, Vinylhalide- or Acyl-Substituted Quaternary Carbon Stereogenic Centers through NHC−Cu-Catalyzed Enantioselective Conjugate Additions of Si-Containing Vinylaluminums to β-Substituted Cyclic Enones

Journal of the American Chemical Society ◽

10.1021/ja110054q ◽

2011 ◽

Vol 133 (4) ◽

pp. 736-739 ◽

Cited By ~ 112

Author(s):

Tricia L. May ◽

Jennifer A. Dabrowski ◽

Amir H. Hoveyda

Keyword(s):

Quaternary Carbon ◽

Conjugate Additions ◽

Stereogenic Centers ◽

Cyclic Enones

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Catalytic Enantioselective Alkylations of Tetrasubstituted Olefins. Synthesis of All-Carbon Quaternary Stereogenic Centers Through Cu-Catalyzed Asymmetric Conjugate Additions of Alkylzinc Reagents to Enones.

ChemInform ◽

10.1002/chin.200609071 ◽

2006 ◽

Vol 37 (9) ◽

Author(s):

Alexander W. Hird ◽

Amir H. Hoveyda

Keyword(s):

Conjugate Additions ◽

Stereogenic Centers ◽

Tetrasubstituted Olefins ◽

Quaternary Stereogenic Centers

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Enantioselective Synthesis of Nitroalkanes Bearing All-Carbon Quaternary Stereogenic Centers through Cu-Catalyzed Asymmetric Conjugate Additions

Journal of the American Chemical Society ◽

10.1021/ja050800f ◽

2005 ◽

Vol 127 (13) ◽

pp. 4584-4585 ◽

Cited By ~ 123

Author(s):

Jing Wu ◽

Dawn M. Mampreian ◽

Amir H. Hoveyda

Keyword(s):

Enantioselective Synthesis ◽

Conjugate Additions ◽

Stereogenic Centers ◽

Quaternary Stereogenic Centers

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Enantioselective Synthesis of Boron-Substituted Quaternary Carbon Stereogenic Centers through NHC-Catalyzed Conjugate Additions of (Pinacolato)boron Units to Enones

Angewandte Chemie International Edition ◽

10.1002/anie.201309982 ◽

2014 ◽

Vol 53 (13) ◽

pp. 3387-3391 ◽

Cited By ~ 75

Author(s):

Suttipol Radomkit ◽

Amir H. Hoveyda

Keyword(s):

Enantioselective Synthesis ◽

Quaternary Carbon ◽

Conjugate Additions ◽

Stereogenic Centers

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Enantioselective Synthesis of Nitroalkanes Bearing All-Carbon Quaternary Stereogenic Centers Through Cu-Catalyzed Asymmetric Conjugate Additions.

ChemInform ◽

10.1002/chin.200533035 ◽

2005 ◽

Vol 36 (33) ◽

Author(s):

Jing Wu ◽

Dawn M. Mampreian ◽

Amir H. Hoveyda

Keyword(s):

Enantioselective Synthesis ◽

Conjugate Additions ◽

Stereogenic Centers ◽

Quaternary Stereogenic Centers

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Generation and Conjugate Additions ofo-Quinone Methides Under Mild Base Conditions: Rapid Synthesis ofN-Substituted Aryl Glycine Derivatives

European Journal of Organic Chemistry ◽

10.1002/ejoc.201301018 ◽

2013 ◽

Vol 2013 (36) ◽

pp. 8299-8306 ◽

Cited By ~ 5

Author(s):

Wei Wang ◽

Zhong Zheng ◽

Xiangmin Wang ◽

Jinchun Chen

Keyword(s):

Quinone Methides ◽

Rapid Synthesis ◽

Conjugate Additions ◽

Glycine Derivatives

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