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Literature DB >> 18582043

A chiral rhodium carboxamidate catalyst for enantioselective C-H amination.

Abstract

Rh2(S-nap)4, a chiral dirhodium tetracarboxamidate complex, has been developed and shown to be an effective catalyst for the asymmetric, intramolecular C-H amination of sulfamate esters. Enantiomeric excesses range from 60-99% for a collection of disparately substituted 3-arylpropylsulfamates. In addition, Rh2(S-nap)4 is found to promote chemoselective allylic C-H oxidation of unsaturated sulfamates, a property not observed with other dirhodium complexes tested to date.

Entities: Chemical Gene

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Year: 2008 PMID： 18582043 PMCID： PMC2597189 DOI： 10.1021/ja8031955

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

7 in total

1. Efficient diastereoselective intermolecular rhodium-catalyzed C-H amination.

Authors: Chungen Liang; Fabien Robert-Peillard; Corinne Fruit; Paul Müller; Robert H Dodd; Philippe Dauban
Journal: Angew Chem Int Ed Engl Date: 2006-07-10 Impact factor: 15.336

2. Highly diastereo- and enantioselective intramolecular amidation of saturated C-H bonds catalyzed by ruthenium porphyrins.

Authors: Jiang-Lin Liang; Shi-Xue Yuan; Jie-Sheng Huang; Wing-Yiu Yu; Chi-Ming Che
Journal: Angew Chem Int Ed Engl Date: 2002-09-16 Impact factor: 15.336

3. A DFT study on the mechanism of Rh2(II,II)-catalyzed intramolecular amidation of carbamates.

Authors: Xufeng Lin; Cunyuan Zhao; Chi-Ming Che; Zhuofeng Ke; David Lee Phillips
Journal: Chem Asian J Date: 2007-09-03

4. Perspective on dirhodium carboxamidates as catalysts.

Authors: Michael P Doyle
Journal: J Org Chem Date: 2006-12-08 Impact factor: 4.354

5. Toward a synthetically useful stereoselective C-H amination of hydrocarbons.

Authors: Chungen Liang; Florence Collet; Fabien Robert-Peillard; Paul Müller; Robert H Dodd; Philippe Dauban
Journal: J Am Chem Soc Date: 2007-12-12 Impact factor: 15.419

Review 6. Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion.

Authors: Huw M L Davies; James R Manning
Journal: Nature Date: 2008-01-24 Impact factor: 49.962

7. Analogues of 2'(3')-O-L-phenylalanyladenosine as substrates and inhibitors of ribosomal peptidyltransferase.

Authors: J Zemlicka; A Bhuta; P Bhuta
Journal: J Med Chem Date: 1983-02 Impact factor: 7.446

7 in total

43 in total

1. Ruthenium-catalyzed γ-carbolinium ion formation from aryl azides; synthesis of dimebolin.

Authors: Huijun Dong; Regina T Latka; Tom G Driver
Journal: Org Lett Date: 2011-04-25 Impact factor: 6.005

2. Selective intermolecular amination of C-H bonds at tertiary carbon centers.

Authors: Jennifer L Roizen; David N Zalatan; J Du Bois
Journal: Angew Chem Int Ed Engl Date: 2013-09-02 Impact factor: 15.336

3. An enzymatic platform for the asymmetric amination of primary, secondary and tertiary C(sp³)-H bonds.

Authors: Yang Yang; Inha Cho; Xiaotian Qi; Peng Liu; Frances H Arnold
Journal: Nat Chem Date: 2019-10-14 Impact factor: 24.427

4. Chemo- and Enantioselective Intramolecular Silver-Catalyzed Aziridinations.

Authors: Minsoo Ju; Cale D Weatherly; Ilia A Guzei; Jennifer M Schomaker
Journal: Angew Chem Int Ed Engl Date: 2017-07-12 Impact factor: 15.336

5. Application of diazene-directed fragment assembly to the total synthesis and stereochemical assignment of (+)-desmethyl-meso-chimonanthine and related heterodimeric alkaloids.

Authors: Stephen P Lathrop; Mohammad Movassaghi
Journal: Chem Sci Date: 2014-01-01 Impact factor: 9.825

6. Ir-Catalyzed Intermolecular Branch-Selective Allylic C-H Amidation of Unactivated Terminal Olefins.

Authors: Honghui Lei; Tomislav Rovis
Journal: J Am Chem Soc Date: 2019-02-04 Impact factor: 15.419

Review 7. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors: John C K Chu; Tomislav Rovis
Journal: Angew Chem Int Ed Engl Date: 2017-12-05 Impact factor: 15.336

A chiral rhodium carboxamidate catalyst for enantioselective C-H amination.

1. Efficient diastereoselective intermolecular rhodium-catalyzed C-H amination.

2. Highly diastereo- and enantioselective intramolecular amidation of saturated C-H bonds catalyzed by ruthenium porphyrins.

3. A DFT study on the mechanism of Rh2(II,II)-catalyzed intramolecular amidation of carbamates.

4. Perspective on dirhodium carboxamidates as catalysts.

5. Toward a synthetically useful stereoselective C-H amination of hydrocarbons.

Review 6. Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion.

7. Analogues of 2'(3')-O-L-phenylalanyladenosine as substrates and inhibitors of ribosomal peptidyltransferase.

1. Ruthenium-catalyzed γ-carbolinium ion formation from aryl azides; synthesis of dimebolin.

2. Selective intermolecular amination of C-H bonds at tertiary carbon centers.

3. An enzymatic platform for the asymmetric amination of primary, secondary and tertiary C(sp³)-H bonds.

4. Chemo- and Enantioselective Intramolecular Silver-Catalyzed Aziridinations.

5. Application of diazene-directed fragment assembly to the total synthesis and stereochemical assignment of (+)-desmethyl-meso-chimonanthine and related heterodimeric alkaloids.

6. Ir-Catalyzed Intermolecular Branch-Selective Allylic C-H Amidation of Unactivated Terminal Olefins.

Review 7. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

8. Room-temperature enantioselective C-H iodination via kinetic resolution.

9. Rh(2)(II)-catalyzed synthesis of carbazoles from biaryl azides.

10. Pd(II)-catalyzed enantioselective C-H olefination of diphenylacetic acids.

Review 6. Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion.

Review 7. Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Review 7. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.