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Literature DB >> 21942742

Highly diastereoselective and general synthesis of primary β-fluoroamines.

Abstract

A short, high yielding protocol has been developed for the highly diastereoselective (dr >20:1) and general synthesis of primary β-fluoroamines by the enantioselective α-fluorination of aldehydes, conversion into the N-sulfinyl aldimine, nucleophilic addition of various organometallic species, and 1° amine liberation.

Entities: Chemical Species

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Year: 2011 PMID： 21942742 PMCID： PMC3196525 DOI： 10.1021/ol202415j

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

17 in total

1. Beta-fluoroamphetamines via the stereoselective synthesis of benzylic fluorides.

Authors: Alexander J Cresswell; Stephen G Davies; James A Lee; Paul M Roberts; Angela J Russell; James E Thomson; Melloney J Tyte
Journal: Org Lett Date: 2010-07-02 Impact factor: 6.005

2. A highly efficient and direct approach for synthesis of enantiopure beta-amino alcohols by reductive cross-coupling of chiral N-tert-butanesulfinyl imines with aldehydes.

Authors: Yu-Wu Zhong; Yi-Zhou Dong; Kai Fang; Kenji Izumi; Ming-Hua Xu; Guo-Qiang Lin
Journal: J Am Chem Soc Date: 2005-08-31 Impact factor: 15.419

3. A room-temperature protocol for the rhodium(I)-catalyzed addition of arylboron compounds to sulfinimines.

Authors: Yuri Bolshan; Robert A Batey
Journal: Org Lett Date: 2005-04-14 Impact factor: 6.005

4. Enantioselective organocatalytic alpha-fluorination of aldehydes.

Authors: Teresa D Beeson; David W C Macmillan
Journal: J Am Chem Soc Date: 2005-06-22 Impact factor: 15.419

5. Diastereoselective and enantioselective Rh(I)-catalyzed additions of arylboronic acids to N-tert-butanesulfinyl and N-diphenylphosphinoyl aldimines.

Authors: Daniel J Weix; Yili Shi; Jonathan A Ellman
Journal: J Am Chem Soc Date: 2005-02-02 Impact factor: 15.419

6. Highly efficient diastereoselective reduction of alpha-fluoroimines.

Authors: Roy M Malamakal; Whitney R Hess; Todd A Davis
Journal: Org Lett Date: 2010-05-21 Impact factor: 6.005

7. A rapid and general method for the asymmetric synthesis of 2-substituted pyrrolidines using tert-butanesulfinamide.

Authors: Kristin M Brinner; Jonathan A Ellman
Journal: Org Biomol Chem Date: 2005-05-04 Impact factor: 3.876

Review 8. Fluorine in medicinal chemistry.

Authors: Hans-Joachim Böhm; David Banner; Stefanie Bendels; Manfred Kansy; Bernd Kuhn; Klaus Müller; Ulrike Obst-Sander; Martin Stahl
Journal: Chembiochem Date: 2004-05-03 Impact factor: 3.164

Review 9. Predicting and tuning physicochemical properties in lead optimization: amine basicities.

Authors: Martin Morgenthaler; Eliane Schweizer; Anja Hoffmann-Röder; Fausta Benini; Rainer E Martin; Georg Jaeschke; Björn Wagner; Holger Fischer; Stefanie Bendels; Daniel Zimmerli; Josef Schneider; François Diederich; Manfred Kansy; Klaus Müller
Journal: ChemMedChem Date: 2007-08 Impact factor: 3.466

10. Asymmetric synthesis of beta-amino acid derivatives incorporating a broad range of substitution patterns by enolate additions to tert-butanesulfinyl imines.

Authors: Tony P Tang; Jonathan A Ellman
Journal: J Org Chem Date: 2002-11-01 Impact factor: 4.354

10 in total

1. A general, enantioselective synthesis of protected morpholines and piperazines.

Authors: Matthew C O'Reilly; Craig W Lindsley
Journal: Org Lett Date: 2012-05-22 Impact factor: 6.005

2. A versatile enantioselective synthesis of azabicyclic ring systems: a concise total synthesis of (+)-grandisine D and unnatural analogues.

Authors: Olugbeminiyi O Fadeyi; Timothy J Senter; Kristopher N Hahn; Craig W Lindsley
Journal: Chemistry Date: 2012-03-30 Impact factor: 5.236

3. Enantioselective total synthesis of (+)-amabiline.

Authors: Timothy J Senter; Olugbeminiyi O Fadeyi; Craig W Lindsley
Journal: Org Lett Date: 2012-03-20 Impact factor: 6.005

4. Synthesis and Biological Evaluation of Cremastrine and an Unnatural Analogue.

Authors: Kristopher N Hahn; Olugbeminiyi O Fadeyi; Hyekyung P Cho; Craig W Lindsley
Journal: Tetrahedron Lett Date: 2012-05-10 Impact factor: 2.415

5. Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized Olefins Using Fluoride Ion.

Authors: Deng-Fu Lu; Cheng-Liang Zhu; Jeffrey D Sears; Hao Xu
Journal: J Am Chem Soc Date: 2016-08-26 Impact factor: 15.419

6. α-Tetrasubstituted Aldehydes through Electronic and Strain-Controlled Branch-Selective Stereoselective Hydroformylation.

Authors: Josephine Eshon; Floriana Foarta; Clark R Landis; Jennifer M Schomaker
Journal: J Org Chem Date: 2018-08-17 Impact factor: 4.354

7. A General, Enantioselective Synthesis of 1-Azabicyclo[m.n.0]alkane Ring Systems.

Authors: Timothy J Senter; Michael L Schulte; Leah C Konkol; Tyler E Wadzinski; Craig W Lindsley
Journal: Tetrahedron Lett Date: 2013-03-27 Impact factor: 2.415

8. Enantioselective synthesis of C2-functionalized, N-protected morpholines and orthogonally N,N'-protected piperazines via organocatalysis.

Authors: Matthew C O'Reilly; Craig W Lindsley
Journal: Tetrahedron Lett Date: 2011-12-29 Impact factor: 2.415

9. Catalytic Diastereo- and Enantioselective Fluoroamination of Alkenes.

Authors: Katrina M Mennie; Steven M Banik; Elaine C Reichert; Eric N Jacobsen
Journal: J Am Chem Soc Date: 2018-03-29 Impact factor: 15.419

10. A general, enantioselective synthesis of β- and γ-fluoroamines.

Authors: Matthew C O'Reilly; Craig W Lindsley
Journal: Tetrahedron Lett Date: 2013-07-10 Impact factor: 2.415

10 in total