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

Journal Article (Journal Article)

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.

Full Text

Duke Authors

Cited Authors

  • Onyeagusi, CI; Malcolmson, SJ

Published Date

  • November 2020

Published In

Volume / Issue

  • 10 / 21

Start / End Page

  • 12507 - 12536

PubMed ID

  • 34306806

Pubmed Central ID

  • PMC8302206

Electronic International Standard Serial Number (EISSN)

  • 2155-5435

International Standard Serial Number (ISSN)

  • 2155-5435

Digital Object Identifier (DOI)

  • 10.1021/acscatal.0c03569

Language

  • eng