Highly diastereoselective synthesis of enantioenriched anti-α-allyl-β-fluoroamines-Reference-Cited by-同舟云学术

Highly diastereoselective synthesis of enantioenriched anti-α-allyl-β-fluoroamines

Published:2019 Issue:43 Volume:55 Page:6050-6053
ISSN:1359-7345
Container-title:Chemical Communications
language:en
Short-container-title:Chem. Commun.

Author:

Chevis Philip J.¹²³⁴,Wangngae Sirilak¹²³⁴⁵,Thaima Thanaphat¹²³⁴,Carroll Anthony W.¹²³⁴,Willis Anthony C.⁶⁷⁸⁴,Pattarawarapan Mookda⁵⁹¹⁰¹¹,Pyne Stephen G.¹²³⁴^ORCID

Affiliation:

1. School of Chemistry and Molecular Biosciences

2. University of Wollongong

3. Wollongong

4. Australia

5. Department of Chemistry and Center of Excellence for Innovation in Chemistry

6. Research School of Chemistry

7. Australian National University

8. Canberra

9. Faculty of Science

10. Chiang Mai University

11. Thailand

Abstract

A highly diastereoselective synthesis (dr = 99 : 1 97 : 3) of enantioenriched anti-α-allyl-β-fluoroamines (ee = 86–92%) has been developed involving a highly diastereoselective Petasis allyl borono-Mannich reaction of (S)- or (R)-α-fluoroaldehydes.

Funder

University of Wollongong

Thailand Research Fund

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2019/CC/C9CC02765C

Reference37 articles.

1. Understanding organofluorine chemistry. An introduction to the C–F bond

2. Fluorine in medicinal chemistry

3. The influence of fluorine in asymmetric catalysis

4. Informing Molecular Design by Stereoelectronic Theory: The Fluorine Gauche Effect in Catalysis

5. Discovery of N-((3R,4R)-4-Fluoro-1-(6-((3-methoxy-1-methyl-1H-pyrazol-4-yl)amino)-9-methyl-9H-purin-2-yl)pyrrolidine-3-yl)acrylamide (PF-06747775) through Structure-Based Drug Design: A High Affinity Irreversible Inhibitor Targeting Oncogenic EGFR Mutants with Selectivity over Wild-Type EGFR

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