Diastereoselective Addition of Arylzinc Reagents to Sugar Aldehydes
| Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
|---|---|
| Data(s) |
02/10/2013
02/10/2013
2012
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| Resumo |
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 Et2Zn to generate arylethylzinc reagents. The exquisite reactivity of the arylzinc reagents allowed for an efficient and mild arylation, delivering the corresponding products in diastereolsomeric ratios of up to >20:1. The utility of the methodology is highlighted with an efficient formal synthesis of (+)-7-epl-goniofufurone, a member of the styryllactone family of natural products. FAPESP FAPESP CNPq CNPq FAPERGS FAPERGS CAPES CAPES |
| Identificador |
ORGANIC LETTERS, WASHINGTON, v. 14, n. 15, pp. 3962-3965, AUG 3, 2012 1523-7060 http://www.producao.usp.br/handle/BDPI/33935 10.1021/ol301724x |
| Idioma(s) |
eng |
| Publicador |
AMER CHEMICAL SOC WASHINGTON |
| Relação |
ORGANIC LETTERS |
| Direitos |
closedAccess Copyright AMER CHEMICAL SOC |
| Palavras-Chave | #HIGHLY ENANTIOSELECTIVE ADDITION #GRIGNARD-REAGENTS #STYRYL LACTONES #TITANIUM(IV) CATALYST #ORGANOZINC REAGENTS #CARBONYL-COMPOUNDS #BORONIC ACIDS #D-GLUCOSE #KETONES #ARYLATION #CHEMISTRY, ORGANIC |
| Tipo |
article original article publishedVersion |
