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Literature DB >> 22894680

Stereoselective synthesis of morpholines via copper-promoted oxyamination of alkenes.

Abstract

A new copper(II) 2-ethylhexanoate-promoted addition of an alcohol and an amine across an alkene (oxyamination) is reported. The alcohol addition is intramolecular, while coupling with the amine occurs intermolecularly. Several 2-aminomethyl morpholines were synthesized in good to excellent yields and diastereoselectivities.

Entities: Chemical Gene

Mesh：

Substances：
Alkenes
Morpholines
Copper

Year: 2012 PMID： 22894680 PMCID： PMC3465956 DOI： 10.1021/ol301984b

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

40 in total

1. Construction of tetrahydrofurans by PdII/PdIV-catalyzed aminooxygenation of alkenes.

Authors: Lopa V Desai; Melanie S Sanford
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

2. Copper-promoted and copper-catalyzed intermolecular alkene diamination.

Authors: Fatima C Sequeira; Benjamin W Turnpenny; Sherry R Chemler
Journal: Angew Chem Int Ed Engl Date: 2010-08-23 Impact factor: 15.336

3. Highly regioselective Pd-catalyzed intermolecular aminoacetoxylation of alkenes and evidence for cis-aminopalladation and S(N)2 C-O bond formation.

Authors: Guosheng Liu; Shannon S Stahl
Journal: J Am Chem Soc Date: 2006-06-07 Impact factor: 15.419

4. Copper(II) acetate promoted intramolecular diamination of unactivated olefins.

Authors: Thomas P Zabawa; Dhanalakshmi Kasi; Sherry R Chemler
Journal: J Am Chem Soc Date: 2005-08-17 Impact factor: 15.419

5. Palladium-catalyzed ring-forming aminoacetoxylation of alkenes.

Authors: Erik J Alexanian; Chulbom Lee; Erik J Sorensen
Journal: J Am Chem Soc Date: 2005-06-01 Impact factor: 15.419

6. Intramolecular Pd(II)-catalyzed aerobic oxidative amination of alkenes: synthesis of six-membered N-heterocycles.

Authors: Zhan Lu; Shannon S Stahl
Journal: Org Lett Date: 2012-02-22 Impact factor: 6.005

7. Novel Pd(II)-catalysed N,O-bicyclisation as an efficient route to the 6-oxa-2-azabicyclo[3.2.1]octane skeleton.

Authors: Peter Szolcsányi; Tibor Gracza
Journal: Chem Commun (Camb) Date: 2005-07-04 Impact factor: 6.222

8. Metal-free highly regioselective aminotrifluoroacetoxylation of alkenes.

Authors: Helena M Lovick; Forrest E Michael
Journal: J Am Chem Soc Date: 2010-02-03 Impact factor: 15.419

9. Metal-free oxidative cyclization of urea-tethered alkenes with hypervalent iodine.

Authors: Brian M Cochran; Forrest E Michael
Journal: Org Lett Date: 2008-10-09 Impact factor: 6.005

10. Efficient, stereoselective synthesis of trans-2,5-disubstituted morpholines.

Authors: Brian A Lanman; Andrew G Myers
Journal: Org Lett Date: 2004-03-18 Impact factor: 6.005

14 in total

1. Practical Synthetic Procedures for the Iron-Catalyzed Intermolecular Olefin Aminohydroxylation Using Functionalized Hydroxylamines.

Authors: Cheng-Liang Zhu; Deng-Fu Lu; Jeffrey D Sears; Zhen-Xin Jia; Hao Xu
Journal: Synthesis (Stuttg) Date: 2016-07-25 Impact factor: 3.157

2. Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes.

Authors: Sherry R Chemler; Shuklendu D Karyakarte; Zainab M Khoder
Journal: J Org Chem Date: 2017-09-29 Impact factor: 4.354

3. Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters.

Authors: Barbara J Casavant; Zainab M Khoder; Ilyas A Berhane; Sherry R Chemler
Journal: Org Lett Date: 2015-12-01 Impact factor: 6.005

4. Ligand Controlled Ir-Catalyzed Regiodivergent Oxyamination of Unactivated Alkenes.

Authors: Honghui Lei; John H Conway; Caleb C Cook; Tomislav Rovis
Journal: J Am Chem Soc Date: 2019-07-16 Impact factor: 15.419

5. Copper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers.

Authors: Ilyas A Berhane; Ameya S Burde; Jonathan J Kennedy-Ellis; Eva Zurek; Sherry R Chemler
Journal: Chem Commun (Camb) Date: 2021-09-30 Impact factor: 6.065

6. Copper-catalyzed oxidative Heck reactions between alkyltrifluoroborates and vinyl arenes.

Authors: Timothy W Liwosz; Sherry R Chemler
Journal: Org Lett Date: 2013-06-04 Impact factor: 6.005

Review 7. Catalytic, Stereoselective Dihalogenation of Alkenes: Challenges and Opportunities.

Authors: Alexander J Cresswell; Stanley T-C Eey; Scott E Denmark
Journal: Angew Chem Int Ed Engl Date: 2015-12-02 Impact factor: 15.336

8. Copper-catalyzed enantioselective synthesis of bridged bicyclic ketals from 1,1-disubstituted-4-methylene-1,6-hexanediols and related alkenols.

Authors: Ameya S Burde; Shuklendu D Karyakarte; Eric D Sylvester; Sherry R Chemler
Journal: Chem Commun (Camb) Date: 2021-01-05 Impact factor: 6.222

9. Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes.

Authors: Rong Zhu; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2015-06-23 Impact factor: 15.419

10. Iron(II)-catalyzed intermolecular amino-oxygenation of olefins through the N-O bond cleavage of functionalized hydroxylamines.

Authors: Deng-Fu Lu; Cheng-Liang Zhu; Zhen-Xin Jia; Hao Xu
Journal: J Am Chem Soc Date: 2014-09-16 Impact factor: 15.419