Selective reductive cleavage of 2,3-epoxybromides by the InCl3–NaBH4 reagent system

Ranu, Brindaban C.; Banerjee, Subhash; Das, Arijit

doi:10.1016/j.tetlet.2004.09.120

Cited by 27 publications

(14 citation statements)

References 26 publications

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“…In a similar way, the reduction of the bromo moiety of 2,3-epoxybromides was followed by selective carbon-oxygen bond cleavage to afford the corresponding allylic alcohols. 135 The combination of a catalytic amount of indium(III) chloride and sodium borohydride in acetonitrile was found to reduce, with transposition, the hydroxyl group of Baylis-Hillman adducts 93 (Scheme 42). This remarkably chemoselective reduction which afforded exclusively the E-isomers 94 was applied to the synthesis of two alarm pheromones.…”

Section: Hydroindation From Sodium Borohydride and Indium(iii) Chloridementioning

confidence: 99%

Recent Advances in Indium-Promoted Organic Reactions

Augé¹,

Lubin‐Germain²,

Uziel³

2007

Synthesis

162

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I n d i u m -P r o m o t e d O r g a n i c R e a c t i o n sAbstract: This review deals with organic reactions which are promoted by indium metal or indium salts, with a focus on recent advances in stoichiometric and catalytic pathways. Applications to transmetalations, cross-coupling reactions and carboindation, in which an organoindium species may be postulated, are highlighted, as well as the reactions in which a radical is the key intermediate. Special attention is placed on the role of indium metal as a reducer, and on the Lewis acidity of indium salts in catalytic processes.

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Section: Hydroindation From Sodium Borohydride and Indium(iii) Chloridementioning

confidence: 99%

Recent Advances in Indium-Promoted Organic Reactions

Augé¹,

Lubin‐Germain²,

Uziel³

2007

Synthesis

162

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“…113 2,3-Epoxy bromides have been reduced to allylic alcohols with NaBH 4 and a catalytic amount of InCl 3 (20 mol %) in 50-85% yields (eq 20). 114 (20) Other Reductions. The reductive removal of 2-oxazolidinone chiral auxiliaries with NaBH 4 is a mild and chemoselective method that provided the corresponding alcohols in good to excellent yields (75-95%), with complete preservation of stereochem-istry (>99% ee).…”

Section: Nikola Stiasni and Martin Hiersemannmentioning

confidence: 99%

Sodium Borohydride

Banfi

Narisano

Riva

et al. 2014

Encyclopedia of Reagents for Organic Synthesis

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“…53 This method was based on the reduction of the bromide moiety followed by selective C-O bond cleavage through a radical process. The experimental procedure of this method is very simple: a solution of NaBH 4 and a catalytic amount of indium(III) chloride were added to a solution of the corresponding 2,3-epoxybromides, 66, in anhydrous acetonitrile.…”

Section: Reduction Of Epoxy Compoundsmentioning

confidence: 99%

Recent methodologies mediated by sodium borohydride in the reduction of different classes of compounds

Souza

Vasconcelos

2006

Applied Organom Chemis

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Reduction is a fundamental transformation in organic synthesis. Since its discovery by Brown and co-workers, sodium borohydride is the most frequently hydride used in reduction processes. Owing to the importance of this reagent in modern organic synthesis, the aim of this review is to highlight recent methodologies (2000-2006) mediated by sodium borohydride in the reduction of different classes of compounds. REDUCTION OF ALDEHYDES AND KETONESChadha and Kumar have developed a simple and efficient one-pot reaction for reduction and transesterification of β-keto esters, 1, under mild conditions to produce the

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Selective reductive cleavage of 2,3-epoxybromides by the InCl3–NaBH4 reagent system

Cited by 27 publications

References 26 publications

Recent Advances in Indium-Promoted Organic Reactions

Recent Advances in Indium-Promoted Organic Reactions

Sodium Borohydride

Recent methodologies mediated by sodium borohydride in the reduction of different classes of compounds

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