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Literature DB >> 22468962

A single step approach to piperidines via Ni-catalyzed β-carbon elimination.

Abstract

An easy and expeditious route to substituted piperidines is described. A Ni-phosphine complex was used as catalyst for [4 + 2] cycloaddition of 3-azetidinone and alkynes. The reaction has broad substrate scope and affords piperidines in excellent yields and excellent regioselectivity. In the reaction of an enantiopure azetidinone, complete retention of stereochemistry was observed.

Entities: Chemical Gene

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Year: 2012 PMID： 22468962 PMCID： PMC4138124 DOI： 10.1021/ol300534j

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

16 in total

Review 1. Synthesis of pyridine and dihydropyridine derivatives by regio- and stereoselective addition to N-activated pyridines.

Authors: James A Bull; James J Mousseau; Guillaume Pelletier; André B Charette
Journal: Chem Rev Date: 2012-02-21 Impact factor: 60.622

2. AlMe3-promoted oxidative cyclization of eta2-alkene and eta2-ketone on nickel(0). Observation of intermediate in methyl transfer process.

Authors: Sensuke Ogoshi; Mizu Ueta; Tomoya Arai; Hideo Kurosawa
Journal: J Am Chem Soc Date: 2005-09-21 Impact factor: 15.419

3. Highly enantioselective direct reductive coupling of conjugated alkynes and alpha-ketoesters via rhodium-catalyzed asymmetric hydrogenation.

Authors: Jong-Rock Kong; Ming-Yu Ngai; Michael J Krische
Journal: J Am Chem Soc Date: 2006-01-25 Impact factor: 15.419

4. Application of the aza-Achmatowicz oxidative rearrangement for the stereoselective synthesis of the Cassia and Prosopis alkaloid family.

Authors: Carolyn A Leverett; Michael P Cassidy; Albert Padwa
Journal: J Org Chem Date: 2006-10-27 Impact factor: 4.354

5. A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes.

Authors: Hasnain A Malik; Grant J Sormunen; John Montgomery
Journal: J Am Chem Soc Date: 2010-05-12 Impact factor: 15.419

6. Nickel-catalyzed intermolecular alkyne insertion into cyclobutanones.

Authors: Masahiro Murakami; Shinji Ashida; Takanori Matsuda
Journal: J Am Chem Soc Date: 2005-05-18 Impact factor: 15.419

7. Highly regioselective, catalytic asymmetric reductive coupling of 1,3-enynes and ketones.

Authors: Karen M Miller; Timothy F Jamison
Journal: Org Lett Date: 2005-07-07 Impact factor: 6.005

8. Regioselective cycloaddition of 3-azetidinones and 3-oxetanones with alkynes through nickel-catalysed carbon-carbon bond activation.

Authors: Kelvin Y T Ho; Christophe Aïssa
Journal: Chemistry Date: 2012-02-22 Impact factor: 5.236

9. Enantioselective (formal) aza-Diels-Alder reactions with non-Danishefsky-type dienes.

Authors: Uttam K Tambar; Sharon K Lee; James L Leighton
Journal: J Am Chem Soc Date: 2010-08-04 Impact factor: 15.419

10. Catalytic asymmetric reductive coupling of alkynes and aldehydes: enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones.

Authors: Karen M Miller; Wei-Sheng Huang; Timothy F Jamison
Journal: J Am Chem Soc Date: 2003-03-26 Impact factor: 15.419

12 in total

1. An expeditious route to eight-membered heterocycles by nickel-catalyzed cycloaddition: low-temperature C(sp)2-C(sp)3 bond cleavage.

Authors: Puneet Kumar; Kainan Zhang; Janis Louie
Journal: Angew Chem Int Ed Engl Date: 2012-07-17 Impact factor: 15.336

2. Ruthenium-catalyzed insertion of adjacent diol carbon atoms into C-C bonds: Entry to type II polyketides.

Authors: Matthias Bender; Ben W H Turnbull; Brett R Ambler; Michael J Krische
Journal: Science Date: 2017-08-25 Impact factor: 47.728

3. Nickel-Catalyzed Chemo- and Enantioselective Coupling between Cyclobutanones and Allenes: Rapid Synthesis of [3.2.2] Bicycles.

Authors: Xuan Zhou; Guangbin Dong
Journal: Angew Chem Int Ed Engl Date: 2016-11-04 Impact factor: 15.336

4. Rapid Construction of (-)-Paroxetine and (-)-Femoxetine via N-Heterocyclic Carbene Catalyzed Homoenolate Addition to Nitroalkenes.

Authors: Nicholas A White; Kerem E Ozboya; Darrin M Flanigan; Tomislav Rovis
Journal: Asian J Org Chem Date: 2014-04 Impact factor: 3.319

5. Nickel-catalyzed cycloaddition of 1,3-dienes with 3-azetidinones and 3-oxetanones.

Authors: Ashish Thakur; Megan E Facer; Janis Louie
Journal: Angew Chem Int Ed Engl Date: 2013-09-23 Impact factor: 15.336

6. The iron-catalyzed construction of 2-aminopyrimidines from alkynenitriles and cyanamides.

Authors: Timothy K Lane; Minh H Nguyen; Brendan R D'Souza; Nathan A Spahn; Janis Louie
Journal: Chem Commun (Camb) Date: 2013-09-11 Impact factor: 6.222

7. A catalytic asymmetric synthesis of polysubstituted piperidines using a rhodium(I)-catalyzed [2+2+2] cycloaddition employing a cleavable tether.

Authors: Timothy J Martin; Tomislav Rovis
Journal: Angew Chem Int Ed Engl Date: 2013-04-19 Impact factor: 15.336

Review 8. Ruthenium(0)-Catalyzed Cycloaddition of 1,2-Diols, Ketols, or Diones via Alcohol-Mediated Hydrogen Transfer.

Authors: Hiroki Sato; Ben W H Turnbull; Keisuke Fukaya; Michael J Krische
Journal: Angew Chem Int Ed Engl Date: 2018-02-06 Impact factor: 15.336

9. Fused-Ring Formation by an Intramolecular "Cut-and-Sew" Reaction between Cyclobutanones and Alkynes.

Authors: Lin Deng; Likun Jin; Guangbin Dong
Journal: Angew Chem Int Ed Engl Date: 2018-02-06 Impact factor: 15.336

10. Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction.

Authors: Brett R Ambler; Ben W H Turnbull; Sankar Rao Suravarapu; Maulen M Uteuliyev; Nancy O Huynh; Michael J Krische
Journal: J Am Chem Soc Date: 2018-07-11 Impact factor: 15.419