Development of an Asymmetric Hydrogenation Route to (<i>S</i>)-<i>N</i>-Boc-2,6-dimethyltyrosine

Praquin, Céline; Koning, Pieter D. de; Peach, Philip; Howard, Roger M.; Spencer, Sarah L.

doi:10.1021/op200065p

Cited by 25 publications

(10 citation statements)

References 10 publications

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“…It relied on the enantioselective hydrogenation of the sterically encumbered b-aryl-substituted acrylate 13. 66 A low catalyst loading (0.20 mol%; S/C = 500) of a rhodium complex of the ferrocenyl diphosphine (S,S)-Et-FerroTANE sufficed to fully reduce the congested alkene 13 under optimised reaction conditions. The resultant Dmt-protected derivative 14 was isolated in 95% yield and with 93% ee.…”

Section: Enantioselective Hydrogenation Of Acrylate Derivativesmentioning

confidence: 99%

Rhodium-catalysed asymmetric hydrogenation as a valuable synthetic tool for the preparation of chiral drugs

2013

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During the last few decades, rhodium-catalysed asymmetric hydrogenation of diverse alkene classes has emerged as a powerful synthetic tool in the pharmaceutical industry, contributing to the manufacturing of chiral drugs, recent drug candidates for clinical trials, and major synthetic precursors of drugs. Numerous efficient chiral rhodium complexes, most of which are derived from enantiopure phosphorus ligands, have been employed for the preparation of chiral drugs and intermediates thereof. This review article is intended to provide an updated overview of the most striking contributions in this field, organised according to substrate class: acrylate derivatives, itaconate derivatives, α-substituted enamides, α-arylenol acetates, and minimally functionalised olefins.

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Section: Enantioselective Hydrogenation Of Acrylate Derivativesmentioning

confidence: 99%

Rhodium-catalysed asymmetric hydrogenation as a valuable synthetic tool for the preparation of chiral drugs

2013

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“…We therefore turned to precursor 1 a as a substitute of 3methyl-6-vinyl tetrazine and explored an in situ elimination-Heck cascade reaction. [12] We initially screened the reaction conditions for the Heck cascade reaction of 1 a with iodobenzene using common catalysts, ligands, bases, and solvents. However, using 1.5 equiv iodobenzene, 10 % [Pd(PPh 3 ) 4 ]/Et 3 N/DMF and heating to 80 8C for 90 min, led to no observable product (Table 1, entry 1).…”

mentioning

confidence: 99%

In Situ Synthesis of Alkenyl Tetrazines for Highly Fluorogenic Bioorthogonal Live‐Cell Imaging Probes

et al. 2014

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In spite of the wide application potential of 1,2,4,5-tetrazines, particularly in live-cell and in-vivo imaging, a major limitation has been the lack of practical synthetic methods. Here we report the in situ synthesis of (E)-3-substituted-6-alkenyl-1,2,4,5-tetrazine derivatives via an elimination-Heck cascade reaction. Using this strategy, we provide 24 examples of π-conjugated tetrazine derivatives that can be conveniently prepared from tetrazine building blocks and related halides. These include tetrazine analogs of biological small molecules, highly conjugated buta-1,3-diene substituted tetrazines, and a diverse array of fluorescent probes suitable for live-cell imaging. These highly conjugated probes show dramatic fluorescent turn-on (up to 400-fold) when reacted with dienophiles such as cyclopropenes and trans-cyclooctenes, and we demonstrate their application for live-cell imaging. This work provides an efficient and practical synthetic methodology for tetrazine derivatives and will facilitate the application of conjugated tetrazines, particularly as fluorogenic probes for live-cell imaging.

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“…19,11 The applications of P-chirogenic and P-chirotopic organophosphorus compounds concern agrochemistry, 1 medicinal drugs 2 or biomolecules, 3 ligands 20 or organocatalysts 21 in asymmetric reactions, chiral coordinating polymers 22 or counter-ions, 9,11 rhodium complex and P-chirogenic diphosphines 14 or 18 has also been the subject of substantial industrial developments to produce amino acid derivatives 16 or 20 respectively, having a therapeutic interest (Scheme 1). 23,24 Therefore interest in P-chirogenic organophosphorus compounds has greatly expanded in recent past years, due to the development of new efficient stereoselective synthetic methods, using mainly menthol, ephedrine, sparteine or a-arylethylamine as chiral auxiliaries. 20, 25 On the other hand, the use of borane as P(III)-protecting group of the tricoordinated organophosphorus compounds has also resulted in significant breakthroughs in their asymmetric synthesis.…”

Section: Introductionmentioning

confidence: 99%

Designing P*-chirogenic Organophosphorus Compounds: from Ligands to Organocatalysts

Jugé

2015

Phosphorus, Sulfur, and Silicon and the Related Elements

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The interest of organophosphorus compounds bearing chirality on the phosphorus atom has greatly expanded in last decade, due to the development of efficient stereoselective synthetic methods, using menthol, ephedrine, sparteine or a-arylethylamine as chiral auxiliaries, and phosphine borane chemistry. Today, the efficient design of P-chirogenic organophosphorus compounds can be achieved using electrophilic or nucleophilic stereoselective reactions at the Pcentre, to afford a large variety of derivatives with P*-C, P*-H, P*-Cl, P*-O, or P*-N bond formation. Recent progress of the ephedrine methodology was illustrated by the enantiodivergent synthesis of new classes of P-chirogenic ligands, phosphonium salts or organocatalysts, and their uses for the preparation of chiral coordinating polymers and clusters, or in asymmetric catalyzed and organocatalyzed reactions.

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Development of an Asymmetric Hydrogenation Route to (S)-N-Boc-2,6-dimethyltyrosine

Cited by 25 publications

References 10 publications

Rhodium-catalysed asymmetric hydrogenation as a valuable synthetic tool for the preparation of chiral drugs

Rhodium-catalysed asymmetric hydrogenation as a valuable synthetic tool for the preparation of chiral drugs

In Situ Synthesis of Alkenyl Tetrazines for Highly Fluorogenic Bioorthogonal Live‐Cell Imaging Probes

Designing P*-chirogenic Organophosphorus Compounds: from Ligands to Organocatalysts

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