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Literature DB >> 26509757

Regio- and Stereospecific 1,3-Allyl Group Transfer Triggered by a Copper-Catalyzed Borylation/ortho-Cyanation Cascade.

Abstract

A copper-catalyzed borylation/ortho-cyanation/allyl group transfer cascade was developed. Initiated by an unconventional copper-catalyzed electrophilic dearomatization, this process features regio- and stereospecific 1,3-transposition of the allyl fragment enabled by an aromatization-driven Cope rearrangement. This method provides an effective means for the construction of adjacent tertiary and quaternary stereocenters with excellent diastereocontrol.

Entities: Chemical Disease

Keywords: CC activation; copper; cyanation; dearomatization; sigmatropic rearrangement

Mesh：

Substances：

Year: 2015 PMID： 26509757 PMCID： PMC4754675 DOI： 10.1002/anie.201508294

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

34 in total

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3. Transition metal chemistry of cyclopropenes and cyclopropanes.

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4. A Highly Active Catalyst for the Room-Temperature Amination and Suzuki Coupling of Aryl Chlorides.

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5. Stereospecific synthesis of cyclobutylboronates through copper(I)-catalyzed reaction of homoallylic sulfonates and a diboron derivative.

Authors: Hajime Ito; Takashi Toyoda; Masaya Sawamura
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6. Metal-arene interactions in dialkylbiarylphosphane complexes of copper, silver, and gold.

Authors: Patricia Pérez-Galán; Nicolas Delpont; Elena Herrero-Gómez; Feliu Maseras; Antonio M Echavarren
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7. Rhodium-catalyzed directed C-H cyanation of arenes with N-cyano-N-phenyl-p-toluenesulfonamide.

Authors: Tian-Jun Gong; Bin Xiao; Wan-Min Cheng; Wei Su; Jun Xu; Zhao-Jing Liu; Lei Liu; Yao Fu
Journal: J Am Chem Soc Date: 2013-07-12 Impact factor: 15.419

8. Cyclobutanes in catalysis.

Authors: Tobias Seiser; Tanguy Saget; Duc N Tran; Nicolai Cramer
Journal: Angew Chem Int Ed Engl Date: 2011-07-26 Impact factor: 15.336

9. Formal Asymmetric Hydrobromination of Styrenes via Copper-Catalyzed 1,3-Halogen Migration.

Authors: R J Van Hoveln; S C Schmid; M Tretbar; C T Buttke; J M Schomaker
Journal: Chem Sci Date: 2014-12-01 Impact factor: 9.825

10. NHC-catalyzed ring expansion of oxacycloalkane-2-carboxaldehydes: a versatile synthesis of lactones.

Authors: Li Wang; Karen Thai; Michel Gravel
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4 in total

1. Evidence for Simultaneous Dearomatization of Two Aromatic Rings under Mild Conditions in Cu(I)-Catalyzed Direct Asymmetric Dearomatization of Pyridine.

Authors: Michael W Gribble; Richard Y Liu; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2020-06-11 Impact factor: 15.419