Domino transformation of D-glucal to racemic alpha-substituted alpha-hydroxymethyl furfuryl derivatives.
Lewis acid mediated one-pot transformation of D-glucal in the presence of nucleophiles leads to the formation of racemic alpha-substituted alpha-hydroxymethyl furfuryl derivatives, versatile synthons for biologically active molecules. Transformations using O-, S-, C-, and N-nucleophiles could be achieved readily under mild and scalable conditions. Indium triflate proved to be the catalyst of choice in terms of conversion and regioselectivity.
Mukherjee
Debaraj
D
Bio-organic Chemistry Division, Indian Institute of Integrative Medicine (CSIR), Canal Road, Jammu, India-180001.
Yousuf
Syed Khalid
SK
Taneja
Subhash Chandra
SC
D000588:Amines / Q000737:chemistry; D002125:Calcium Gluconate / Q000737:chemistry*; D005662:Furaldehyde / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry
D000588:Amines; D010636:Phenols; C008046:5-hydroxymethylfurfural; D005662:Furaldehyde; D002125:Calcium Gluconate