Binaphthol-Catalyzed Asymmetric Conjugate Arylboration of Enones

Turner, H. McNeill; Patel, Jignesh J.; Niljianskul, Nootaree; Chong, J. Michael

doi:10.1021/ol202391r

Cited by 66 publications

(38 citation statements)

References 44 publications

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“…Other publications patents are based on very close two approaches [57][58][59][60][61][62][63][64][65] which propose asymmetric hydrogenation of [57][58][59][60][61][62][63][64] or enantioselective synthesis of [65] (Scheme 14.4.). …”

Section: Tolterodine-detrolmentioning

confidence: 99%

Anticholinergic Drugs

Vardanyan

Hruby

2016

Synthesis of Best-Seller Drugs

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Section: Tolterodine-detrolmentioning

confidence: 99%

Anticholinergic Drugs

Vardanyan

Hruby

2016

Synthesis of Best-Seller Drugs

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“…Our primary results have been published, 22 although there is only one example in our paper (Scheme 6). Similarly, in 2011, Michael used 5 to the conjugate addition of arylboronates to α,β-unsaturated ketones with enantioselectivities of up to 99:1 (Scheme 7), 23 and above all, this method was applied to synthesize intermediates for syntheses of (+)-indatraline and (+)-tolterodine. Zhang and coworkers synthesized 6 for the first time in 2013, and used it for asymmetric methallylation of ketones.…”

Section: Binols 33′-disubstituted By Acyclic Functional Groupsmentioning

confidence: 99%

BINOLs modified at 3, 3′-positions: chemists’ preferred choice in asymmetric catalysis

Li¹,

Liu²,

Wu³

2015

Arkivoc

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This article provides a general overview of the most relevant topics in the applications of BINOL modified at the 3 and 3′-positions in asymmetric catalysis. A brief introduction to the chiral BINOL backbone so modified is given. A selection of the most outstanding uses of the catalysts according to the functional groups at the 3,3′-positions of BINOL backbones such as 3,3′-disubstituents of BINOLs, phosphoric acid derivatives and phosphoramidites is then presented. This review aims to introduce the latest developments of this active field, including the literature since 2008.

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“…As can be seen from this example, there is a substantial need for analytical methods that enable a reliable and precise determination of the enantiopurity even of highly enantioenriched indatraline samples. Of course, such methods will also be valuable tools for the preparation of the indatraline enantiomers, independent of whether this is accomplished by a resolution via crystallization (by formation of diastereomers) as described by Bøgesø et al,2 or by asymmetric synthesis applying chiral catalysts [8][9][10][11][12][13] or chiral functional group transfer reagents. 14 So far, only two methods for the characterization of the enantiopurity of indatraline enantiomers have been described in the literature.…”

Section: Introductionmentioning

confidence: 99%

Enantiopurity Determination of the Enantiomers of the Triple Reuptake Inhibitor Indatraline

et al. 2013

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The present study describes the development of two approaches for the determination of the enantiopurity of both enantiomers of indatraline. Initially, a method was developed using different chiral solvating agents (CSAs) for diastereomeric discrimination regarding signal separation in (1)H nuclear magnetic resonance (NMR) spectroscopy, revealing MTPA as a promising choice for the differentiation of the indatraline enantiomers. This CSA was also tested for its ideal molar ratio, temperature, and solvent. Optimized conditions could be achieved that made determination of enantiopurity for (1R,3S)-indatraline up to 98.9% enantiomeric excess (ee) possible. To quantify even higher enantiopurities, a high-performance liquid chromatography (HPLC) method based on a modified β-cyclodextrine phase was established. The influence of buffer type, concentration, pH value, percentage and kind of organic modifier, temperature, injection volume as well as sample solvent on chromatographic parameters was investigated. Afterwards, the reliability of the established HPLC method was demonstrated by validation according to the ICH guideline Q2(R1) regarding specificity, accuracy, precision, linearity, and quantitation limit. The developed method proved to be strictly linear within a concentration range of 1.25-1000 μM for the (1R,3S)-enantiomer and 1.25-750 μM for its mirror image that enables a reliable determination of enantiopurities up to 99.75% ee for the (1R,3S)-enantiomer and up to 99.67% ee for the (1S,3R)-enantiomer.

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Binaphthol-Catalyzed Asymmetric Conjugate Arylboration of Enones

Cited by 66 publications

References 44 publications

Anticholinergic Drugs

Anticholinergic Drugs

BINOLs modified at 3, 3′-positions: chemists’ preferred choice in asymmetric catalysis

Enantiopurity Determination of the Enantiomers of the Triple Reuptake Inhibitor Indatraline

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