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Gold(III) Chloride Catalyzed Synthesis of Chiral Substituted 3-formyl Furans From Carbohydrates: Application in the Synthesis of 1,5-dicarbonyl Derivatives and furo[3,2-c]pyridine

Gold(III) Chloride Catalyzed Synthesis of Chiral Substituted 3-formyl Furans From Carbohydrates: Application in the Synthesis of 1,5-dicarbonyl Derivatives and furo[3,2-c]pyridine

Kanchan Mal, Abhinandan Sharma, Indrajit Das

Chemistry. 2014 Sep 8;20(37):11932-45.

PMID: 25077819

Abstract:

This report describes a gold(III)-catalyzed efficient general route to densely substituted chiral 3-formyl furans under extremely mild conditions from suitably protected 5-(1-alkynyl)-2,3-dihydropyran-4-one using H2 O as a nucleophile. The reaction proceeds through the initial formation of an activated alkyne-gold(III) complex intermediate, followed by either a domino nucleophilic attack/anti-endo-dig cyclization, or the formation of a cyclic oxonium ion with subsequent attack by H2 O. To confirm the proposed mechanistic pathway, we employed MeOH as a nucleophile instead of H2 O to result in a substituted furo[3,2-c]pyran derivative, as anticipated. The similar furo[3,2-c]pyran skeleton with a hybrid carbohydrate-furan derivative has also been achieved through pyridinium dichromate (PDC) oxidation of a substituted chiral 3-formyl furan. The corresponding protected 5-(1-alkynyl)-2,3-dihydropyran-4-one can be synthesized from the monosaccharides (both hexoses and pentose) following oxidation, iodination, and Sonogashira coupling sequences. Furthermore, to demonstrate the potentiality of chiral 3-formyl furan derivatives, a TiBr4 -catalyzed reaction of these derivatives has been shown to offer efficient access to 1,5-dicarbonyl compounds, which on treatment with NH4 OAc in slightly acidic conditions afforded substituted furo[3,2-c]pyridine.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP13453071	Gold(III) chloride		13453-07-1	Price

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