Direct reductive amination and selective 1,2-reduction of α,β-unsaturated aldehydes and ketones by NaBH4 using H3PW12O40 as catalyst

Heydari, Akbar; Khaksar, Samad; Âkbari, Jafar; Esfandyari, Maryam; Pourayoubi, Mehrdad; Tajbakhsh, Mahmood

doi:10.1016/j.tetlet.2006.12.069

Cited by 64 publications

(29 citation statements)

References 38 publications

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“…However, this can only happen if Pic-BH 3 has reducing power over ketones. This activity was reported for other aminoboranes, 7 but not for Pic-BH 3 .…”

Section: 13supporting

confidence: 49%

“…Sodium triacetoxyborohydride (NaBH 3 (OAc)) 6 has also been employed, but mostly in non-protic solvents, since in methanol or water it reduces the carbonyl groups, decomposes, and gives flammable subproducts. 7 Pyridine borane (Pyr-BH 3 ) [8][9][10] was the most representative aminoborane employed, but it is unstable, and decomposes causing fire; even explosions were reported.…”

Section: Introductionmentioning

confidence: 99%

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Usage of α-picoline borane for the reductive amination of carbohydrates

Navarro¹,

Stortz²

2011

Arkivoc

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, to recognize their achievements in organic chemistry and their contributions in the development of the field in Argentina AbstractThe reaction of reductive amination, widely used for carbohydrates, was reviewed in our lab, especially in the context of the analytical determination of carbohydrate enantiomers. The best conditions for the technique have been evaluated, showing that under optimal working conditions it is possible to use α-picoline borane as a reducing agent instead of sodium cyanoborohydride without affecting the selectivity or the yield. The main reason for the variation of the technique was that, in the presence of acetic acid, secondary epimeric products were produced with α-picoline borane due to an Amadori rearrangement. This new modification assures lower toxicity, and thus a more environmental-friendly reaction system. Preparative scale synthesis can also be efficiently made with this reducing reagent.

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“…However, this can only happen if Pic-BH 3 has reducing power over ketones. This activity was reported for other aminoboranes, 7 but not for Pic-BH 3 .…”

Section: 13supporting

confidence: 49%

Section: Introductionmentioning

confidence: 99%

Usage of α-picoline borane for the reductive amination of carbohydrates

Navarro¹,

Stortz²

2011

Arkivoc

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“…a,b-Unsaturated aldehydes and ketones could be easily converted into the corresponding allyl alcohols 59 by reaction with H 3 PW 12 O 40 (0.5 mol%)/NaBH 4 (Scheme 58) [166].…”

Section: Scheme 57mentioning

confidence: 99%

Recent developments in use of heteropolyacids, their salts and polyoxometalates in organic synthesis

Heravi

Sadjadi

2009

JICS

111

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Heteropolyacids, their salts and polyoxometalates have been used as catalysts in wide range of organic reactions such as multi components, oxidation, reductions, electrochemical and photochemical reactions. There have been tremendous and continued efforts to modify the catalytic performance of heteropoly acids such as supporting them on MCM, silica gel, etc. In this review, we have attempted to bring some of new applications of heteropolyacids in organic reactions and recent approaches on modifying them, into focus.

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“…In addition to the reductive amination catalyzed by the transition metals [2], boranes [3] and borohydrides [4], an organocatalytic approach is a promising method to obtain amine compounds [1]. In the organocatalytic approach, trichlorosilane and Hantzsch dihydropyridine were separately used as reducing agents for the reduction of imines in the presence of organocatalyst.…”

Section: Introductionmentioning

confidence: 99%

Carbohydrate-Derived Organocatalysts for the Reduction of Imines with Trichlorosilane

Ge¹,

Qian²,

Chen³

2015

MSCE

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The backbone of D-glucosamine hydrochloride was fine-tuned and modified by protecting the hydroxyl groups. In order to reduce imines with trichlorosilane, the carbohydrate-derived organocatalysts were prepared and screened. Methyl-4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyr anoside was found as the best catalyst. The reduction was proceeded under CHCl3 as solvent at 40˚C, affording 68% -94% yield.

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Direct reductive amination and selective 1,2-reduction of α,β-unsaturated aldehydes and ketones by NaBH4 using H3PW12O40 as catalyst

Cited by 64 publications

References 38 publications

Usage of α-picoline borane for the reductive amination of carbohydrates

Usage of α-picoline borane for the reductive amination of carbohydrates

Recent developments in use of heteropolyacids, their salts and polyoxometalates in organic synthesis

Carbohydrate-Derived Organocatalysts for the Reduction of Imines with Trichlorosilane

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