Total Regio- and Diastereocontrol in the Aldol Reactions of Dienolborinates

Ramachandran, P. Veeraraghavan; Nicponski, Daniel R.; Kim, Bomi

doi:10.1021/ol400381q

Cited by 22 publications

(21 citation statements)

References 50 publications

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“…Moisture-and/or oxygen-sensitive reactions were conducted using common Schlenk techniques. The synthesis of MIDA, 48 4-(6-methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl) benzoic acid, 40 trimethylphosphine, 49,50 and ethyl 3-butenoate 51 were performed according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Liquid Crystalline Benzoic Acid Ester MIDA Boronates: Synthesis and Mesomorphic Properties

2020

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Two series of N-methyliminodiacetic acid (MIDA) boronates were prepared and their mesomorphic properties were investigated. MIDA-substituted benzoic acid esters were synthesized via the Mitsunobu reaction. The second series of MIDA benzyl ether derivatives was prepared via Williamson etherification and subsequent borylation. Both series exhibit smectic A (SmA) phases. In the case of MIDA boronate esters, a substitution with perfluorinated side chains led to increased transition temperatures and broadening of the SmA phases. The phase geometries of the mesophases were determined by X-ray diffraction. Quantum-chemical calculations provided further insight into the packing model.

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Section: Methodsmentioning

confidence: 99%

Liquid Crystalline Benzoic Acid Ester MIDA Boronates: Synthesis and Mesomorphic Properties

2020

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“…Ethyl but-3-enolate was synthesized following the published procedure [29]. Briefly, pentane (5 mL) was placed in a 50 mL round bottle flask with ethanol (863 μL) and trimethylamine (1.34 mL) under 0 °C.…”

Section: Methodsmentioning

confidence: 99%

“…The organic solution was further dried by sodium sulfate before the removal of solvent using rotary evaporation. The purity and structure of the obtained product were confirmed according to the characterization data in the literature [29].…”

Section: Methodsmentioning

confidence: 99%

Alkanethiolate-Capped Palladium Nanoparticles for Regio- and Stereoselective Hydrogenation of Allenes

Chen

Shon

2018

Catalysts

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Colloidal Pd nanoparticles capped with octanethiolate ligands have previously shown an excellent selectivity toward the mono-hydrogenation of both isolated and conjugated dienes to internal alkenes. This paper reports an efficient stereoselective mono-hydrogenation of cumulated dienes (allenes) to either Z or E olefinic isomers, depending on the substitution pattern around C=C bonds. Kinetic studies indicate that the reaction progresses through the hydrogenation of less hindered C=C bonds to produce internal Z olefinic isomers. In the cases of di-substitued olefinic products, this initial hydrogenation step is followed by the subsequent isomerization of Z to E isomers. In contrast, the slow isomerization of Z to E isomers for tri-substituted olefinic products results in the preservation of Z stereochemistry. The high selectivity of Pd nanoparticles averting an additional hydrogenation is steered from the controlled electronic and geometric properties of the Pd surface, which are the result of thiolate-induced partial poisoning and surface crowding, respectively. The high activity of colloidal Pd nanoparticle catalysts allows the reactions to be completed at room temperature and atmospheric pressure.

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“…[2][3][4] In contrast, highly diastereo-and enantioselective syntheses of the anti-diastereomers via aldol (and related) reactions are generally lacking. 5 We recently reported 6 a highly diastereoselective synthesis of syn-b-hydroxy-a-vinyl carboxylic esters 4 with good enantioselectivity via the reductive aldol reaction of allenyl ester 1 with 10-trimethylsilyl-9-borabicyclo[3.3.2]decane (2R, Soderquist's borane) (Fig. 1a).…”

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confidence: 99%

Enantio- and diastereoselective synthesis of syn -β-hydroxy-α-alkenyl carboxamides via reductive aldol reactions of morpholine 4-methyl-2,3-pentadienoic carboxamide with diisopinocampheylborane

Hilali

Roush

2015

Tetrahedron Letters

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Total Regio- and Diastereocontrol in the Aldol Reactions of Dienolborinates

Cited by 22 publications

References 50 publications

Liquid Crystalline Benzoic Acid Ester MIDA Boronates: Synthesis and Mesomorphic Properties

Liquid Crystalline Benzoic Acid Ester MIDA Boronates: Synthesis and Mesomorphic Properties

Alkanethiolate-Capped Palladium Nanoparticles for Regio- and Stereoselective Hydrogenation of Allenes

Enantio- and diastereoselective synthesis of syn -β-hydroxy-α-alkenyl carboxamides via reductive aldol reactions of morpholine 4-methyl-2,3-pentadienoic carboxamide with diisopinocampheylborane

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