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Literature DB >> 14653683

Stereochemical models for rh-catalyzed amination reactions of chiral sulfamates.

Abstract

Oxidative C-H amination of chiral sulfamate esters using achiral Rh-carboxylate catalysts, PhI(OAc)(2), and MgO occurs in high yield and with good to excellent diastereocontrol. A number of examples are included to support a proposed transition state model that accounts for the observed stereoinduction. In addition, stereoselective intramolecular aziridination with substituted homoallyl sulfamates is demonstrated and is rationalized through an analogous stereochemical construct. [reaction: see text]

Entities: Chemical

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Year: 2003 PMID： 14653683 DOI： 10.1021/ol035776u

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

17 in total

1. A stereoselective synthesis of the bromopyrrole natural product (-)-agelastatin A.

Authors: Paul M Wehn; J Du Bois
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

2. 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

3. Synthesis and reactivity of unique heterocyclic structures en route to substituted diamines.

Authors: David E Olson; Autumn Maruniak; Sushant Malhotra; Barry M Trost; J Du Bois
Journal: Org Lett Date: 2011-05-27 Impact factor: 6.005

Review 4. 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

Stereochemical models for rh-catalyzed amination reactions of chiral sulfamates.

1. A stereoselective synthesis of the bromopyrrole natural product (-)-agelastatin A.

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

3. Synthesis and reactivity of unique heterocyclic structures en route to substituted diamines.

Review 4. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

5. Rhodium-Catalyzed C-H Amination - An Enabling Method for Chemical Synthesis.

6. Metal-catalyzed nitrogen-atom transfer methods for the oxidation of aliphatic C-H bonds.

7. Rh2(II)-catalyzed intramolecular aliphatic C-H bond amination reactions using aryl azides as the N-atom source.

8. Synthesis of 1,3-diamines through rhodium-catalyzed C-H insertion.

9. Palladium-catalysed C-H activation of aliphatic amines to give strained nitrogen heterocycles.

10. Oxidative Cyclization of Sulfamate Esters Using NaOCl - A Metal-Mediated Hoffman-Löffler Freytag Reaction.

Review 4. Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Review 4. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.