2017
DOI: 10.1016/j.jfluchem.2016.12.008
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Catalytic asymmetric synthesis of 2,3,3,3-tetrafluoro-2-methyl-1-arylpropan-1-amines as useful building blocks for SAR-studies

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Cited by 20 publications
(9 citation statements)
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“…In Scheme 31, the radical deoxygenation followed by Boc-removal and amide formation is described for two cases (106 and 107), with three steps and 52−57% overall yields of the reduction products. It is worth noting that with PhOC(S)O derivatization, the purification from byproducts revealed to be tedious, prompting to study a solution that was found with the imidazolyl substituent converted by TTMSS (3 equiv) and AIBN (0.3 equiv) in anhydrous toluene at 85 °C for 2.5 h. 100 Another deoxygenation process used in medicinal chemistry was described in the synthesis of analogues of adrenostatic drugs such as metyrapone 109, to study competitive inhibitors against their binding to rat adrenal membranes, especially mitochondria membranes, thus impairing the oxidation metabolism of corticosteroids. The intermediate xanthogenate 108 was converted with TTMSS/AIBN in dry toluene at 90 °C in 55% yield of product 109 (Scheme 32).…”
Section: Deoxygenation Of Alcoholsmentioning
confidence: 99%
“…In Scheme 31, the radical deoxygenation followed by Boc-removal and amide formation is described for two cases (106 and 107), with three steps and 52−57% overall yields of the reduction products. It is worth noting that with PhOC(S)O derivatization, the purification from byproducts revealed to be tedious, prompting to study a solution that was found with the imidazolyl substituent converted by TTMSS (3 equiv) and AIBN (0.3 equiv) in anhydrous toluene at 85 °C for 2.5 h. 100 Another deoxygenation process used in medicinal chemistry was described in the synthesis of analogues of adrenostatic drugs such as metyrapone 109, to study competitive inhibitors against their binding to rat adrenal membranes, especially mitochondria membranes, thus impairing the oxidation metabolism of corticosteroids. The intermediate xanthogenate 108 was converted with TTMSS/AIBN in dry toluene at 90 °C in 55% yield of product 109 (Scheme 32).…”
Section: Deoxygenation Of Alcoholsmentioning
confidence: 99%
“…Although we developed a Mannich-type reaction of α-hydroxy- N -acetylpyrrole utilizing N - o -Ts imines as electrophiles via In­(III) catalysis, there is much room for improvement toward practical organic synthesis; i.e., low catalytic turnover (≤4.9), moderate diastereoselectivity, and difficult removal of the o -Ts group on the nitrogen (Figure c) . In our continuing program of enolization chemistry using 7-azaindoline amides, α-oxygen functionalized amides has remained elusive, despite the successful implementation of α-alkyl-, fluoroalkyl-, nitrogen-, thio-, and halo-functionalized amides . Herein, we document the successful incorporation of α-oxygen functionalized 7-azaindoline amide into a direct Mannich manifold, delivering syn -configured β-amino-α-hydroxy amides (Figure d).…”
mentioning
confidence: 90%
“…Shibasaki and co‐workers reported that 7‐azaindoline amides, including α‐halo derivatives, behaved as latent enolates under the action of a cooperative catalytic system consisting of a soft Lewis acid and a hard Brønsted base . Catalytic amounts of the Cu(I)/Barton's base binary system was widely effective for generating the corresponding Cu(I)‐enolates which were formidable nucleophiles to forge C−C connectivity through Mannich‐type reaction with both aromatic and aliphatic imine electrophiles (Scheme ).…”
Section: Intermolecular α‐Alkylation Of α‐Haloamidesmentioning
confidence: 99%
“…Moreover, the obtained 7‐azaindoline amide derivatives, similarly to Weinreb amides, could take part to functional group interconversion reactions leading to high‐value compounds with halogens on a stereogenic carbon. As an example, 2,3,3,3‐tetrafluoro‐2‐methyl‐1‐arylpropan‐1‐amines D , to be used as fluorinated surrogates for α‐isopropylbenzylamines in SAR‐studies, were efficiently prepared reacting the 7‐azaindoline amide A with N ‐Boc protected aryl imines B (Scheme ) …”
Section: Intermolecular α‐Alkylation Of α‐Haloamidesmentioning
confidence: 99%