Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc-pyrrolidine

9
Enantioselective, Pallad ium-Catalyzed α-Arylatio n of N-Boc-pyrrolidine Kevin R. Campos J. Am. Chem. Soc. 2006, 128, 3538-3539

description

Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc-pyrrolidine. Kevin R. Campos J. Am. Chem. Soc. 2006 , 128 , 3538-3539. 2-Arylpyrrolidines. Biologically active compounds as neuronal nicotinic acetylcholine receptor. Effective controllers in asymmetric synthesis. - PowerPoint PPT Presentation

Transcript of Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc-pyrrolidine

Page 1: Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc-pyrrolidine

Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc-pyrroli

dine

Kevin R. Campos

J. Am. Chem. Soc. 2006, 128, 3538-3539

Page 2: Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc-pyrrolidine

2-Arylpyrrolidines

•Biologically active compounds as neuronal nicotinic acetylcholine receptor.

•Effective controllers in asymmetric synthesis.

Page 3: Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc-pyrrolidine
Page 4: Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc-pyrrolidine
Page 5: Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc-pyrrolidine
Page 6: Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc-pyrrolidine
Page 7: Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc-pyrrolidine
Page 8: Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc-pyrrolidine
Page 9: Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc-pyrrolidine

Conclusions

• The enantioselective deprotonation/transmetalation/Negishi coupling was found to be quite general, affording a diverse array of 2-arylpyrrolidines in good yield and 96:4 er.

• This sequence offers a number of advantages over existing methods and represents the most convenient and practical synthesis of enantiomerically enriched 2-arylpyrrolidines and 2,5-diarylpyrrolidines.


BOC EUROPEAN EQUITY FUND OF FUNDS · 2020. 8. 31. · Οκτωβρίου 2017 και ξεκίνησε δραστηριότητες την 1η Ιανουαρίου 2018. Η κύρια

BOC EUROPEAN EQUITY FUND OF FUNDS · 2020. 8. 31. · Οκτωβρίου 2017 και ξεκίνησε δραστηριότητες την 1η Ιανουαρίου 2018. Η κύρια

VBOC1(α) Generalized Multidimensional …current BOC modulation waveforms and offer an opportunity to our readers to understand signal design “secrets” I invented the variable

VBOC1(α) Generalized Multidimensional …current BOC modulation waveforms and offer an opportunity to our readers to understand signal design “secrets” I invented the variable

Exploring New Partners for the Domino α-Arylation/Michael ...diposit.ub.edu/dspace/bitstream/2445/127810/1/667423.pdf · FULL PAPER Exploring New Partners for the Domino α-Arylation/Michael

Exploring New Partners for the Domino α-Arylation/Michael ...diposit.ub.edu/dspace/bitstream/2445/127810/1/667423.pdf · FULL PAPER Exploring New Partners for the Domino α-Arylation/Michael

Direct α-Arylation of Ketones 958 Seminars_pdf/FS03_SS04...Direct α-Arylation of Ketones Zhensheng Ding January 29, 2003 Department of Chemistry Michigan State University

Direct α-Arylation of Ketones 958 Seminars_pdf/FS03_SS04...Direct α-Arylation of Ketones Zhensheng Ding January 29, 2003 Department of Chemistry Michigan State University

Decarboxylative Arylation of α Amino Acids via Photoredox …chemlabs.princeton.edu/macmillan/wp-content/uploads/... · 2014-02-15 · of amine α-functionalization capabilities,

Decarboxylative Arylation of α Amino Acids via Photoredox …chemlabs.princeton.edu/macmillan/wp-content/uploads/... · 2014-02-15 · of amine α-functionalization capabilities,

© Ivyspring International Publisher. All rights reserved ... › v07p0326.pdfN-Boc-1,3-diaminopropane (2 mmol) and TEA (2 mmol) in 10 ml CH 2Cl 2 was slowly added at 0-5°C. The resulting

© Ivyspring International Publisher. All rights reserved ... › v07p0326.pdfN-Boc-1,3-diaminopropane (2 mmol) and TEA (2 mmol) in 10 ml CH 2Cl 2 was slowly added at 0-5°C. The resulting

Chemistry Letters€¦ · dium(II) Complexes with Tridentate N-Heterocyclic Carbene Ligands Containing Aryloxy Groups and Their Application to Heck Reaction Cl1 N1 Pd1 O1 C1 Palladium

Chemistry Letters€¦ · dium(II) Complexes with Tridentate N-Heterocyclic Carbene Ligands Containing Aryloxy Groups and Their Application to Heck Reaction Cl1 N1 Pd1 O1 C1 Palladium

Synthesis of Diverse β-Quaternary Ketones via … of Diverse β-Quaternary Ketones via Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic ... 30.4 29.596 Chiralcel

Synthesis of Diverse β-Quaternary Ketones via … of Diverse β-Quaternary Ketones via Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic ... 30.4 29.596 Chiralcel

C. The Synthetic & Mechanistic Organic Chemistry of …ccc.chem.pitt.edu/wipf/Courses/2320_06-files/IIC_Organo...1 C. The Synthetic & Mechanistic Organic Chemistry of Palladium - Heck

C. The Synthetic & Mechanistic Organic Chemistry of …ccc.chem.pitt.edu/wipf/Courses/2320_06-files/IIC_Organo...1 C. The Synthetic & Mechanistic Organic Chemistry of Palladium - Heck

Colloidal submicron-palladium particles stabilized with ...Palladium particles were synthesized as follows. 100 cm3 ethanol solution including 20 mg palladium acetate was mixed with

Colloidal submicron-palladium particles stabilized with ...Palladium particles were synthesized as follows. 100 cm3 ethanol solution including 20 mg palladium acetate was mixed with

105. Enantioselective Decarboxylative Arylation of α‐Amino Acids ...

105. Enantioselective Decarboxylative Arylation of α‐Amino Acids ...

Chapter 2 The Elementary Steps in TM Catalysis - UPMC · Anion Capture The nucleophilicaddition at palladium is usually followed by the reductive elimination, and the combination

Chapter 2 The Elementary Steps in TM Catalysis - UPMC · Anion Capture The nucleophilicaddition at palladium is usually followed by the reductive elimination, and the combination

Συν_15 - Απόφαση 04.28.2014 Της Επιτροπής Για Boc - Έρευνα Για Οεδ Copy

Συν_15 - Απόφαση 04.28.2014 Της Επιτροπής Για Boc - Έρευνα Για Οεδ Copy

Photochemicalkeystepsinthe synthesisof+alkaloids...17 Indole Photochemistry intramolecular: N O hυ 92% N H O H H N Boc N H CO2Et EtO2C hυ N Boc NH H CO2Et CO2 Et 82% N Boc N 2 CO2Et

Photochemicalkeystepsinthe synthesisof+alkaloids...17 Indole Photochemistry intramolecular: N O hυ 92% N H O H H N Boc N H CO2Et EtO2C hυ N Boc NH H CO2Et CO2 Et 82% N Boc N 2 CO2Et

-Peptide Chimeras as Novel Antimicrobials · piperidine/DMF. Continuing elongation of the ε-peptide chain was performed by removing Boc-group on ε-Lys, followed by coupling with

-Peptide Chimeras as Novel Antimicrobials · piperidine/DMF. Continuing elongation of the ε-peptide chain was performed by removing Boc-group on ε-Lys, followed by coupling with

Palladium-Catalyzed Decarboxylative alpha-Arylation

Palladium-Catalyzed Decarboxylative alpha-Arylation

Pd-Catalyzed α-Arylation of Sulfones in a Three- Component ...diposit.ub.edu/dspace/bitstream/2445/127808/1/661320.pdf · arylation/Michael addition process based on the use of sulfones

Pd-Catalyzed α-Arylation of Sulfones in a Three- Component ...diposit.ub.edu/dspace/bitstream/2445/127808/1/661320.pdf · arylation/Michael addition process based on the use of sulfones

69451 Weinheim, Germany · 2008. 9. 15. · Table S1 – Initial Screening NHBoc NC CO2Et Cl I CO2Et Cat. (5 mol%) 33% K2CO3 BocHN EtO2C CN EtO2C I N I CN CO2Et Boc O 1.2 equiv. Tol.

69451 Weinheim, Germany · 2008. 9. 15. · Table S1 – Initial Screening NHBoc NC CO2Et Cl I CO2Et Cat. (5 mol%) 33% K2CO3 BocHN EtO2C CN EtO2C I N I CN CO2Et Boc O 1.2 equiv. Tol.

Synthesis of substituted isoquinolines utilizing palladium ... · tioned on the heterocyclic ring of the resulting isoquinoline were investigated (Scheme 2). A range of ketones were

Synthesis of substituted isoquinolines utilizing palladium ... · tioned on the heterocyclic ring of the resulting isoquinoline were investigated (Scheme 2). A range of ketones were

Synthesis of N-Heterocycles via Intramolecular Reductive Cyclizations … · 2012-02-04 · Synthesis of N-Heterocycles via Intramolecular Reductive Cyclizations of ... N-arylation

Synthesis of N-Heterocycles via Intramolecular Reductive Cyclizations … · 2012-02-04 · Synthesis of N-Heterocycles via Intramolecular Reductive Cyclizations of ... N-arylation