Catalytic Enantioselective Friedel−Crafts Reactions of Aromatic Compounds with Glyoxylate:  A Simple Procedure for the Synthesis of Optically Active Aromatic Mandelic Acid Esters

A rhodium-catalyzed enantioselective addition of glyoxylates to arylboronic acids promoted by a simple chiral sulfinamide-based olefin ligand under mild reaction conditions is described. The reaction provides access to a variety of optically active substituted mandelic acid esters in good yields with up to 83% ee. The catalytic system is also applicable to pyruvate addition. The synthetic utility of this method is highlighted by a formal synthesis of the antiplatelet drug clopidogrel.

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ChemInform Abstract: Palladium(0)-Catalyzed Rearrangements of Allylic Sulfoximines to Allyl Sulfinimidic Acid Esters and Optically Active N-Cbz Protected γ-Amino-enones.

ChemInform ◽

10.1002/chin.199905096 ◽

2010 ◽

Vol 30 (5) ◽

pp. no-no

Author(s):

S. G. PYNE ◽

D. M. DAVID ◽

Z. DONG

Keyword(s):

Optically Active ◽

Acid Esters

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Studies on Optically Active Amino Acids. V. Synthesis of Optically Active α-Aminoalcohols by the Reduction of α-Amino Acid Esters with Sodium Borohydride

Chemical and Pharmaceutical Bulletin ◽

10.1248/cpb.13.995 ◽

1965 ◽

Vol 13 (8) ◽

pp. 995-1000 ◽

Cited By ~ 67

Author(s):

Hedeo Seki ◽

Kenji Koga ◽

Hisayuki Matsuo ◽

Sadao Ohki ◽

Ichiro Matsuo ◽

...

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Sodium Borohydride ◽

Optically Active ◽

Amino Acid Esters ◽

Acid Esters

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Convenient Preparation of Optically Active N,N’-Disubstituted Piperazines from Various (S)-α-Amino Acid Esters

Synthesis ◽

10.1055/s-1996-4245 ◽

1996 ◽

Vol 1996 (04) ◽

pp. 452-454 ◽

Cited By ~ 5

Author(s):

Masaaki Watanabe ◽

Yoshitane Kojima ◽

Kenji Kawabe ◽

Eiji Hatamoto ◽

Eiji Tsuru ◽

...

Keyword(s):

Amino Acid ◽

Optically Active ◽

Amino Acid Esters ◽

Convenient Preparation ◽

Acid Esters

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Enantioselective Equilibration−Access to Chiral Aldol Adducts of Mandelic Acid Esters

Organic Letters ◽

10.1021/ol062252w ◽

2006 ◽

Vol 8 (23) ◽

pp. 5353-5355 ◽

Cited By ~ 7

Author(s):

Stefan Scholtis ◽

Andreas Ide ◽

Rainer Mahrwald

Keyword(s):

Mandelic Acid ◽

Acid Esters

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Copper-catalyzed intramolecular redox reaction: Asymmetric synthesis of chiral 2-(1H-pyrrol-1-yl)-mandelic acid esters

Tetrahedron ◽

10.1016/j.tet.2018.11.024 ◽

2018 ◽

Vol 74 (52) ◽

pp. 7480-7484

Author(s):

Hong-Jin Du ◽

Chao Lin ◽

Xiaoan Wen ◽

Qing-Long Xu

Keyword(s):

Asymmetric Synthesis ◽

Redox Reaction ◽

Mandelic Acid ◽

Acid Esters

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Visible-Light-Induced Radical Polynitration of Arylboronic Acids: Synthesis of Polynitrophenols

Synthesis ◽

10.1055/s-0037-1610038 ◽

2018 ◽

Vol 50 (15) ◽

pp. 2891-2896 ◽

Cited By ~ 1

Author(s):

Jinna Song ◽

Xihe Bi ◽

Qi Zhang ◽

Kaki Raveendra Babu ◽

Zhouliang Huang

Keyword(s):

Visible Light ◽

Aromatic Compounds ◽

Functional Group ◽

Simple Procedure ◽

One Pot ◽

Arylboronic Acids ◽

Mild Conditions ◽

Conventional Methods ◽

Straightforward Approach

We report a visible light-assisted one-pot method for the synthesis of polynitrophenols through radical tandem hydroxylation and nitration of arylboronic acids by utilizing copper(II) nitrate trihydrate as the nitro source. This method features mild conditions, a simple procedure, and good functional group tolerance. Compared to conventional methods, this work provides a straightforward approach for the polynitration of aromatic compounds.

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