Multienzymatic Stereoselective Reduction of Tetrasubstituted Cyclic Enones to Halohydrins with Three Contiguous Stereogenic Centers

Silvia Venturi; Elisabetta Brenna; Danilo Colombo; Marco W. Fraaije; Francesco G. Gatti; Piero Macchi; Daniela Monti; Milos Trajkovic; Emilio Zamboni

doi:10.1021/acscatal.0c04097

Multienzymatic Stereoselective Reduction of Tetrasubstituted Cyclic Enones to Halohydrins with Three Contiguous Stereogenic Centers

ACS Catalysis ◽

10.1021/acscatal.0c04097 ◽

2020 ◽

Vol 10 (21) ◽

pp. 13050-13057

Author(s):

Silvia Venturi ◽

Elisabetta Brenna ◽

Danilo Colombo ◽

Marco W. Fraaije ◽

Francesco G. Gatti ◽

...

Keyword(s):

Stereoselective Reduction ◽

Stereogenic Centers ◽

Cyclic Enones

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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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Formation of Quaternary Stereogenic Centers by NHC-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Polyconjugated Cyclic Enones

Chemistry - A European Journal ◽

10.1002/chem.201200502 ◽

2012 ◽

Vol 18 (28) ◽

pp. 8731-8747 ◽

Cited By ~ 69

Author(s):

Matthieu Tissot ◽

Daniele Poggiali ◽

Hélène Hénon ◽

Daniel Müller ◽

Laure Guénée ◽

...

Keyword(s):

Conjugate Addition ◽

Grignard Reagents ◽

Addition Reactions ◽

Stereogenic Centers ◽

Cyclic Enones ◽

Quaternary Stereogenic Centers

Download Full-text

Correction to “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/ja506298x ◽

2014 ◽

Vol 136 (29) ◽

pp. 10544-10544 ◽

Cited By ~ 7

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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A Practical Method for Enantioselective Synthesis of All-Carbon Quaternary Stereogenic Centers Through NHC-Cu-Catalyzed Conjugate Additions of Alkyl- and Arylzinc Reagents to β-Substituted Cyclic Enones.

ChemInform ◽

10.1002/chin.200641024 ◽

2006 ◽

Vol 37 (41) ◽

Author(s):

Kang-sang Lee ◽

M. Kevin Brown ◽

Alexander W. Hird ◽

Amir H. Hoveyda

Keyword(s):

Practical Method ◽

Enantioselective Synthesis ◽

Conjugate Additions ◽

Stereogenic Centers ◽

Cyclic Enones ◽

Quaternary Stereogenic Centers

Download Full-text

ChemInform Abstract: Formation of Quaternary Stereogenic Centers by NHC-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Polyconjugated Cyclic Enones.

ChemInform ◽

10.1002/chin.201245064 ◽

2012 ◽

Vol 43 (45) ◽

pp. no-no

Author(s):

Matthieu Tissot ◽

Daniele Poggiali ◽

Helene Henon ◽

Daniel Mueller ◽

Laure Guenee ◽

...

Keyword(s):

Conjugate Addition ◽

Grignard Reagents ◽

Addition Reactions ◽

Stereogenic Centers ◽

Cyclic Enones ◽

Quaternary Stereogenic Centers

Download Full-text

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 ◽

10.1002/ange.200802910 ◽

2008 ◽

Vol 120 (38) ◽

pp. 7468-7472 ◽

Cited By ~ 57

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

Download Full-text

ChemInform Abstract: 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.

ChemInform ◽

10.1002/chin.201124178 ◽

2011 ◽

Vol 42 (24) ◽

pp. no-no

Author(s):

Tricia L. May ◽

Jennifer A. Dabrowski ◽

Amir H. Hoveyda

Keyword(s):

Quaternary Carbon ◽

Conjugate Additions ◽

Stereogenic Centers ◽

Cyclic Enones

Download Full-text

A Practical Method for Enantioselective Synthesis of All-Carbon Quaternary Stereogenic Centers through NHC-Cu-Catalyzed Conjugate Additions of Alkyl- and Arylzinc Reagents to β-Substituted Cyclic Enones

Journal of the American Chemical Society ◽

10.1021/ja062061o ◽

2006 ◽

Vol 128 (22) ◽

pp. 7182-7184 ◽

Cited By ~ 185

Author(s):

Kang-sang Lee ◽

M. Kevin Brown ◽

Alexander W. Hird ◽

Amir H. Hoveyda

Keyword(s):

Practical Method ◽

Enantioselective Synthesis ◽

Conjugate Additions ◽

Stereogenic Centers ◽

Cyclic Enones ◽

Quaternary Stereogenic Centers

Download Full-text

ChemInform Abstract: 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.

ChemInform ◽

10.1002/chin.200902065 ◽

2009 ◽

Vol 40 (2) ◽

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

Download Full-text