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Literature DB >> 18205371

A mutually pi-facial selective cyclopropanation of chiral enamides using dirhodium(II) carbenoids.

Ting Lu¹, Zhenlei Song, Richard P Hsung.

Abstract

A mutually pi-facial selective cyclopropanation of chiral enamides using dirhodium(II) carbenoids is described here. This work illustrates the influence of enamide substituents on stereoselectivity and reveals insights into this cyclopropanation.

Entities: Chemical

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Year: 2008 PMID： 18205371 DOI： 10.1021/ol702824s

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

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Cited

6 in total

1. A highly regio- and stereoselective synthesis of α-fluorinated imides via fluorination of chiral enamides.

Authors: Yan-Shuang Xu; Yu Tang; He-Jing Feng; Ji-Tian Liu; Richard P Hsung
Journal: Org Lett Date: 2015-01-12 Impact factor: 6.005

2. Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions.

Authors: John B Feltenberger; Ryuji Hayashi; Yu Tang; Eric S C Babiash; Richard P Hsung
Journal: Org Lett Date: 2009-08-20 Impact factor: 6.005

6. Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides.

Authors: Toolika Agrawal; Robert T Martin; Stephen Collins; Zachary Wilhelm; Mytia D Edwards; Osvaldo Gutierrez; Joshua D Sieber
Journal: J Org Chem Date: 2021-03-16 Impact factor: 4.354

6 in total

A mutually pi-facial selective cyclopropanation of chiral enamides using dirhodium(II) carbenoids.

1. A highly regio- and stereoselective synthesis of α-fluorinated imides via fluorination of chiral enamides.

2. Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions.

3. Synthesis of amido-spiro[2.2]pentanes via Simmons-Smith cyclopropanation of allenamides.

4. Highly substituted 2-amido-furans from Rh(II)-catalyzed cyclopropenations of ynamides.

5. Cyclization reactions through DDQ-mediated vinyl oxazolidinone oxidation.

6. Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides.