Diastereoselective addition of arylzinc reagents to sugar aldehydes |
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Authors: | Ana D Wouters Diogo S Lüdtke |
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Affiliation: | Faculdade de Ciências Farmacêuticas, Universidade de S?o Paulo, USP, S?o Paulo, SP, Brazil and Instituto de Química, Universidade Federal do Rio Grande do Sul, UFRGS, Av. Bento Gon?alves 9500, 91501-970, Porto Alegre, RS, Brazil. |
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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. |
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