Gottfried Kinkel im Kreise seiner Jugendfreunde

Enders, Carl

doi:10.1515/9783111653846

Cited by 1 publication

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Initial forays into the stereoselective synthesis of this building block utilized chiral auxiliaries bound to the imino nitrogen atom, 18a,69 but in 2010, the Enders laboratory reported the catalytic enantioselective addition of trimethylsilyl cyanide to N-aryl trifluoromethyl ketimines catalyzed by Takemoto's thiourea 23 in the presence of isopropyl alcohol (Scheme 17, top). [70][71][72] The transformations are highly enantioselective for aryl ketimines regardless of electronics; however, ortho-substituted arenes show poor reactivity. Heteroaromatic, α,β-unsaturated, and aliphatic substrates are viable reaction partners, although these imines all require double the catalyst loading (10 mol %).…”

Section: Strecker Reactionmentioning

confidence: 99%

Strategies for the Catalytic Enantioselective Synthesis of α-Trifluoromethyl Amines

Onyeagusi

Malcolmson

2020

ACS Catal.

View full text Add to dashboard Cite

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-CF 3 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.

show abstract

Section: Strecker Reactionmentioning

confidence: 99%