ChemInform Abstract: Diels‐Alder Reaction of D‐Glucose‐Based Diene with in situ Generated Quinones.

InCl3–CH3CN–H2O: an efficient catalyst-solvent combination for the synthesis of Perlin aldehydes and related compounds. Application in the synthesis of unnatural l-azasugars

“…5,21 Further, a reinvestigation of the oxymercurationedemercuration reaction of glycals by Shaw and coworkers revealed that the reaction was highly solvent (THF vs dioxane) dependent. 21 The only non-mercurial method available as of now for the synthesis of Perlin aldehydes is also due to Shaw and co-workers.…”

“…1 It has been well documented that the presence of a pushepull a,b-unsaturated carbonyl group further enhances the versatility of sugar nuclei as chiral templates in organic synthesis. Examples of such compounds include alkyl-hex-2-eno-uloses, 2 2-C-formyl glycals, 3 2,3-dideoxy-a,b-unsaturated sugar aldehydes 4,5 and other carbohydrate based enones. 6 Since last three decades, 2,3-dideoxy-a,b-unsaturated sugar aldehydes, popularly known as Perlin aldehydes, have been serving as attractive precursors for the synthesis of a wide array of biologically important natural and unnatural compounds.…”

Selective Conversion of Enol Ethers into Alcohols in the Presence of Alkenes Using Hg(OAc)2-NaBH4

“…1,2 We recently reported the use of aqueous Hg(OAc) 2 -NaBH 4 as a mild, non-acidic method for converting alkyl enol ethers into alcohols in one reaction vessel, allowing the survival of a number of acid sensitive protecting groups. 3 Solvomercuration-demercuration has been used to convert glycals to glycosides [4][5][6][7][8] and vinyl ethers to mixed acetals. 9 By analogy, oxymercuration of an alkyl enol ether 1 forms the aacetoxymercurio aldehyde intermediate 2 which, upon in situ treatment with NaBH 4 , undergoes demercuration and reduction of the aldehyde to yield the alcohol 3.…”