45988-04-3Relevant academic research and scientific papers
Regio- and Enantioselective Synthesis of Trifluoromethyl-Substituted Homoallylic α-Tertiary NH2-Amines by Reactions Facilitated by a Threonine-Based Boron-Containing Catalyst
Fager, Diana C.,Hoveyda, Amir H.,Morrison, Ryan J.
, p. 11448 - 11455 (2020/05/25)
A method for catalytic regio- and enantioselective synthesis of trifluoromethyl-substituted and aryl-, heteroaryl-, alkenyl-, and alkynyl-substituted homoallylic α-tertiary NH2-amines is introduced. Easy-to-synthesize and robust N-silyl ketimin
Enantioselective Friedel–Crafts Alkylation Reaction of Heteroarenes with N-Unprotected Trifluoromethyl Ketimines by Means of Chiral Phosphoric Acid
Miyagawa, Masamichi,Yoshida, Masaru,Kiyota, Yuki,Akiyama, Takahiko
supporting information, p. 5677 - 5681 (2019/04/03)
An enantioselective Friedel–Crafts alkylation reaction of pyrroles and indoles with N-unprotected trifluoromethyl ketimines by use of chiral phosphoric acid provided α-trifluoromethylated primary amines bearing chiral tetrasubstituted carbon centers in high yields and with high to excellent enantioselectivities. The present reaction is unique to N-unprotected trifluoromethyl ketimines. No reaction took place with N-p-methoxyphenyl (PMP)-substituted ketimine. Corresponding α-trifluoromethylated amines were transformed without loss of enantioselectivity.
(4-HYDROXYPYRROLIDIN-2-YL)-HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF
-
, (2019/05/15)
The present disclosure relates to bifunctional compounds of formula (I), which can be used as modulators of targeted ubiquitination. In particular, the present disclosure is directed to compounds which contain on one end a VHL ligand moiety, which binds to the VHL E3 ubiquitin ligase, and on the other end a moiety that binds a target protein such that degradation of the target protein/polypeptide is effectuated. Also disclosed are VHL ligands of formula (III).
Enantioselective Rhodium-Catalyzed Addition of Arylboroxines to N-Unprotected Ketimines: Efficient Synthesis of Cipargamin
Zhu, Jinbin,Huang, Linwei,Dong, Wei,Li, Naikai,Yu, Xingxin,Deng, Wei-Ping,Tang, Wenjun
supporting information, p. 16119 - 16123 (2019/11/03)
Highly enantioselective rhodium-catalyzed addition of arylboroxines to N-unprotected ketimines is realized for the first time by employing chiral BIBOP-type ligands with a Rh loading as low as 1 mol %. A range of chiral α-trifluoromethyl-α,α-diaryl α-tertiary amines or 3-amino-3-aryloxindoles were formed with excellent ee values and yields by employing either WingPhos or PFBO-BIBOP as the ligand. The method has enabled an efficient enantioselective synthesis of cipargamin.
Direct access to: N -unprotected tetrasubstituted propargylamines via direct catalytic alkynylation of N -unprotected trifluoromethyl ketimines
Morisaki, Kazuhiro,Morimoto, Hiroyuki,Ohshima, Takashi
supporting information, p. 6319 - 6322 (2017/07/11)
Direct catalytic alkynylation of N-unprotected trifluoromethyl ketimines is reported for the first time. A combination of catalytic amounts of diethylzinc and carboxylic acids promoted the reactions under proton-transfer conditions, allowing an unprecedented direct access to N-unprotected α-tetrasubstituted primary amines without additional deprotection steps.
Unprecedented catalytic asymmetric reduction of N-H imines
Gosselin, Francis,O'Shea, Paul D.,Roy, Stephanie,Reamer, Robert A.,Chen, Cheng-Yi,Volante, Ralph P.
, p. 355 - 358 (2007/10/03)
(Chemical Equation Presented) Addition of lithium bis(trimethylsilyl)amide to perfluorinated ketones 1a-j affords (E)-N-TMS-ketimines 2a-j that are reduced in situ to afford racemic perfluoromethylated amine hydrochloride salts 3a-j in 54-97% yields. Solv
The facile fragmentation of trifluoroacetyl groups to nitriles
Kende, Andrew S.
, p. 4035 - 4038 (2007/10/02)
Trifluoroacetyl groups attached to a carbon atom devoid of hydrogen undergo facile, high-yield conversion to nitriles by reaction with MeAlClNH2, followed by KOtBu, in a 'one-pot' reaction sequence.
α-Amino-α-trifluoromethyl-phenylacetonitrile: A potential reagent for 19F NMR determination of enantiomeric purity of acids
Koos,Mosher
, p. 1541 - 1546 (2007/10/02)
α-Amino-α-trifluoromethyl-phenylacetonitrile, PhC(CF3)(CN)NH2, 2, in which the amino group is located on a crowded, chiral, quaternary carbon center, has been studied as a potential reagent for the 19F NMR determination of enantiomeric purity of chiral acids by conversion to their corresponding diastereomeric amides. The differences in the 19F NMR chemical shifts (Δδ) of the R,R/S,S versus R,S/S,R diastereomeric amides (8a-j) prepared from amine 2 and ten chiral acids range up to 0.266 ppm. Eight of the ten examples have Δδ in excess of the useful minimum of 0.02 ppm. These values are not notably superior to those of other known reagents.
1-(2-HETERYLTHIO)ALKYL ISOCYANATES SYNTHESIS AND REACTIONS WITH PROTON-CONTAINING NUCLEOPHILIC REAGENTS
Vovk, M.V.,Davidyuk, Yu.N.,Samarai, L.I.
, p. 1297 - 1302 (2007/10/02)
The alkylation of benzazoline-2-thiones and quinoline-2-thione by 1-chloroalkyl isocyanates gave 1-(2-heterylthio)alkyl isocyanates.Depending on their nature, the reactions of the products with water, alcohols, phenols, and amines led to the formation of
