2016
DOI: 10.1021/acscatal.6b02456
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Asymmetric Hydrogenation of Allylic Alcohols Using Ir–N,P-Complexes

Abstract: In this study, a series of γ,γ-disubstituted and β,γ-disubstituted allylic alcohols were prepared and successfully hydrogenated using suitable N,P-based Ir complexes. High yields and excellent enantioselectivities were obtained for most of the substrates studied. This investigation also revealed the effect of the acidity of the N,P−Ir-complexes on the acidsensitive allylic alcohols. DFT ΔpK a calculations were used to explain the effect of the N,P-ligand on the acidity of the corresponding Ir-complex. The sele… Show more

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Cited by 39 publications
(27 citation statements)
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“…The basic hydrolysis of 2b in the presence of trichloromethyl group resulted in decomposition. A two-step procedure [19] of esterification and acidic hydrolysis could prepare alcohol 5 in 63% yield. …”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…The basic hydrolysis of 2b in the presence of trichloromethyl group resulted in decomposition. A two-step procedure [19] of esterification and acidic hydrolysis could prepare alcohol 5 in 63% yield. …”
Section: Resultsmentioning
confidence: 99%
“…Column chromatography was generally performed on silica gel (300~400 mesh) and reactions were monitored by thin-layer chromatography (TLC) using 254 nm of UV light to visualize the progress. 1 H NMR (400 MHz), 13 C NMR (100 MHz) and 19 F NMR (376 MHz) were measured on 400M spectrometer. IR spectra were recorded as a thin film on a KBr disk (2 cm diameter) using an FT-IR spectrometer and reported in wavenumbers (cm -1 ).…”
Section: General Informationmentioning
confidence: 99%
“…The stereochemical outcome was again consistent with the quadrant model prediction. 22 The Pfaltz group has studied the asymmetric hydrogenation of an interesting class of functionalized olefins: a,b-unsaturated nitriles. This functional group has been reported to directly coordinate to the Ir-catalyst, and the reduction was found to be successful only when operated under alkaline conditions.…”
Section: Cristiana Margaritamentioning
confidence: 99%
“…Known catalytic approaches to install this subunit often require multistep synthetic sequences via chiral, β-branched carbonyl intermediates, which can hinder the rapid generation of compound libraries for high throughput screening in medicinal chemistry. For example, transition metal-catalyzed asymmetric hydrogenation of α,β-unsaturated acids or esters 12 14 affords the enantiopure β-branched carbonyl intermediates, followed by a reductive amination to install the desired chiral γ-branched amines (Fig. 1b ).…”
Section: Introductionmentioning
confidence: 99%