Chemoselective and Stereoselective Reductions with Modified Borohydride Reagents

Windey, Guy; Seper, Karl W.; Yamamoto, John H.

doi:10.1002/chin.200331283

Cited by 2 publications

(6 citation statements)

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“…The products were purified through column chromatography and the results were presented in Table 1. The results showed that the presence of these metal chloride did not affect the product outcome, instead had increased the yields of compound (2). In all cases, 1,4-addition product was predominate over 1,2-reduction product.…”

Section: Resultsmentioning

confidence: 89%

“…Nor Saliyana et al: STEREOSELECTIVE REDUCTION OF 1-BENZYL-3,3-DIMETHYL-5-METHYLENEPYRROLIDINE-2,4-DIONE USING SODIUM BOROHYDRIDE WITH SELECTED METAL CHLORIDES appropriate reducing agent. Sodium borohydride (NaBH 4 ) is one of the reducing agent which offers good selectivity and have better solubility in most common organic solvents [2]. Its non-hazardous property allow its application in the efficient synthesis of (R)-salmeterol, which used to prevent bronchospasm in asthma patient [1].…”

Section: -2506mentioning

confidence: 99%

“…Its non-hazardous property allow its application in the efficient synthesis of (R)-salmeterol, which used to prevent bronchospasm in asthma patient [1]. It also have been used in industry to synthesized d-Biotin, also known as vitamin H, which is important additional nutrient for humans and animals [2].…”

Section: -2506mentioning

confidence: 99%

“…Two signals for carbonyl carbon at C4 and C4', does not appear in this spectrum. This might be due to rapid tautomerization process between keto and enol form of compound (2), which causes the signals hard to be detected. The enol's quaternary carbon (at C-5'") can be observed at δ 87.57.…”

Section: Figure 1 1 H Nmr Spectra For Reduction Using Nabh 4 Nabh mentioning

confidence: 99%

“…This might be due to the small size of countercations (Mg 2+ and Zn 2+ ) have better coordinating ability which imparts selectivity control during the hydride transfer mechanism [4]. This allows the hydride to transfer mainly on one side only (si-face) and produce compound (2). Meanwhile, big size of countercations cannot perfectly occupy (poor coordinating ability) certain position at a certain time, and thus caused the hydride to transfer equally from both sides (re-or si-face).…”

Section: Figure 1 1 H Nmr Spectra For Reduction Using Nabh 4 Nabh mentioning

confidence: 99%

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Stereoselective Reduction of 1-Benzyl-3,3-Dimethyl-5-Methylenepyrrolidine-2,4-Dione Using Sodium Borohydride With Selected Metal Chlorides

Jumali

Shaameri

Mohamad

et al. 2017

MJAS

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1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione is an intermediate product produced in the synthesis towards the natural bioactive compound, zopfiellamide A. This compound was synthesized via four main steps including dimethylations, addition with CuBr 2 , cyclization with benzylamine and reaction with formaldehyde. The corresponding intermediate was an α,ßunsaturated ketone having exo-alkene group, and it was subjected to reduction using sodium borohydride and selected metal chlorides. In this study, the effect and the hydride transfer mechanism of sodium borohydride-metal chlorides system in the reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione was investigated based on the stereochemical outcome of the product.

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Section: Resultsmentioning

confidence: 89%

Section: -2506mentioning

confidence: 99%

Section: -2506mentioning

confidence: 99%

Section: Figure 1 1 H Nmr Spectra For Reduction Using Nabh 4 Nabh mentioning

confidence: 99%

Section: Figure 1 1 H Nmr Spectra For Reduction Using Nabh 4 Nabh mentioning

confidence: 99%

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Stereoselective Reduction of 1-Benzyl-3,3-Dimethyl-5-Methylenepyrrolidine-2,4-Dione Using Sodium Borohydride With Selected Metal Chlorides

Jumali

Shaameri

Mohamad

et al. 2017

MJAS

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Multijet Oscillating Disc Millireactor: A Novel Approach for Continuous Flow Organic Synthesis

Liguori¹,

Bjørsvik

2011

Org. Process Res. Dev.

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This report discloses proof of concept and experimental results from a project involving design, development, and investigation of a novel approach for flow chemistry and the realization of equipment operating according to this new approach. This device is named multijet oscillating disk (MJOD) reactor and is dedicated to continuous flow organic synthesis in milliscale. Characteristics such as the importance of the multijet disk unit, with or without oscillating, and possible limitations, such as backmixing, have been explored, and the flow system is benchmarked with other technologies. Several well-known reactions and syntheses usefully both in the chemical industry as well as in the research laboratory have been conducted using the new system, which have been benchmarked with batch-and microreactor protocols. In particular the Haloform reaction, the Nef reaction, nucleophilic aromatic substitution, the PaalÀKnorr pyrrole synthesis, sodium borohydride reduction, O-allylation, the Suzuki crosscoupling reaction, the Hofmann rearrangement and N-acylation were performed during the study of the MJOD reactor performance. Our investigations revealed that the MJOD millireactor system can produce various organic compounds at a high rate concomitant with an excellent selectivity. A Hofmann rearrangement was conducted, a reaction that involves handling of a slurry of the substrate. This reaction was successfully conducted, achieving a quantitative conversion into the target molecule.

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Chemoselective and Stereoselective Reductions with Modified Borohydride Reagents

Abstract: Organic chemistryOrganic chemistry Z 0200 Chemoselective and Stereoselective Reductions with Modified Borohydride Reagents -[21 refs.]. -(WINDEY, G.; SEPER, K.; YAMAMOTO, J. H.; PharmaChem 1 (2002) 9, 15-18; Rohm and Haas Co., B-2000 Antwerpen, Belg.; Eng.) -Lindner 31-283

Cited by 2 publications

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Stereoselective Reduction of 1-Benzyl-3,3-Dimethyl-5-Methylenepyrrolidine-2,4-Dione Using Sodium Borohydride With Selected Metal Chlorides

Stereoselective Reduction of 1-Benzyl-3,3-Dimethyl-5-Methylenepyrrolidine-2,4-Dione Using Sodium Borohydride With Selected Metal Chlorides

Multijet Oscillating Disc Millireactor: A Novel Approach for Continuous Flow Organic Synthesis

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