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Strategies for the Catalytic Enantioselective Synthesis of α-Trifluoromethyl Amines.

Publication ,  Journal Article
Onyeagusi, CI; Malcolmson, SJ
Published in: ACS catalysis
November 2020

The exploitation of the α-trifluoromethylamino group as an amide surrogate in peptidomimetics and drug candidates has been on the rise. In a large number of these cases, this moiety bears stereochemistry with the stereochemical identity having important consequences on numerous molecular properties, such as the potency of the compound. Yet, the majority of stereoselective syntheses of α-CF3 amines rely on diastereoselective couplings with chiral reagents. Concurrent with the rapid expansion of fluorine into pharmaceuticals has been the development of catalytic enantioselective means of preparing α-trifluoromethyl amines. In this work, we outline the strategies that have been employed for accessing these enantioenriched amines, including normal polarity approaches and several recent developments in imine umpolung transformations.

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Published In

ACS catalysis

DOI

EISSN

2155-5435

ISSN

2155-5435

Publication Date

November 2020

Volume

10

Issue

21

Start / End Page

12507 / 12536

Related Subject Headings

  • 3406 Physical chemistry
  • 3405 Organic chemistry
  • 3106 Industrial biotechnology
  • 0904 Chemical Engineering
  • 0305 Organic Chemistry
  • 0302 Inorganic Chemistry
 

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Onyeagusi, C. I., & Malcolmson, S. J. (2020). Strategies for the Catalytic Enantioselective Synthesis of α-Trifluoromethyl Amines. ACS Catalysis, 10(21), 12507–12536. https://doi.org/10.1021/acscatal.0c03569
Onyeagusi, Chibueze I., and Steven J. Malcolmson. “Strategies for the Catalytic Enantioselective Synthesis of α-Trifluoromethyl Amines.ACS Catalysis 10, no. 21 (November 2020): 12507–36. https://doi.org/10.1021/acscatal.0c03569.
Onyeagusi CI, Malcolmson SJ. Strategies for the Catalytic Enantioselective Synthesis of α-Trifluoromethyl Amines. ACS catalysis. 2020 Nov;10(21):12507–36.
Onyeagusi, Chibueze I., and Steven J. Malcolmson. “Strategies for the Catalytic Enantioselective Synthesis of α-Trifluoromethyl Amines.ACS Catalysis, vol. 10, no. 21, Nov. 2020, pp. 12507–36. Epmc, doi:10.1021/acscatal.0c03569.
Onyeagusi CI, Malcolmson SJ. Strategies for the Catalytic Enantioselective Synthesis of α-Trifluoromethyl Amines. ACS catalysis. 2020 Nov;10(21):12507–12536.
Journal cover image

Published In

ACS catalysis

DOI

EISSN

2155-5435

ISSN

2155-5435

Publication Date

November 2020

Volume

10

Issue

21

Start / End Page

12507 / 12536

Related Subject Headings

  • 3406 Physical chemistry
  • 3405 Organic chemistry
  • 3106 Industrial biotechnology
  • 0904 Chemical Engineering
  • 0305 Organic Chemistry
  • 0302 Inorganic Chemistry