title: Diastereoselective addition of arylzinc reagents to sugar aldehydes.
abstract: The diastereoselective arylation of sugar-derived aldehydes is described. The arylating reagents are generated in situ by a boron-to-zinc exchange reaction of arylboronic acids with Et(2)Zn to generate arylethylzinc reagents. The exquisite reactivity of the arylzinc reagents allowed for an efficient and mild arylation, delivering the corresponding products in diastereoisomeric ratios of up to >20:1. The utility of the methodology is highlighted with an efficient formal synthesis of (+)-7-epi-goniofufurone, a member of the styryllactone family of natural products.
authors: Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, USP, São Paulo, SP, Brazil.
authors: Ana D
authors: AD
authors: Wouters
authors: Diogo S
authors: DS
authors: Lüdtke
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D002241:Carbohydrates; D007202:Indicators and Reagents; D007783:Lactones; C073080:7-goniofufurone; D015032:Zinc