NDLI: Synthesis of 2,3-Dihydroxyhex-4-enoates by Palladium-Catalyzed Allylic Alkylations of Carbohydrate Derived Vinyl Lactones Palladium Chemistry of Carbohydrate Vinyl Lactones

Content Provider	Semantic Scholar
Author	Singleton, Esther Sahteli, Krishna Hoberg, John O.
Copyright Year	2008
Abstract	SYNTHESIS 2008, No. 22, pp 3682–3686xx.xx.2008 Advanced online publication: 23.10.2008 DOI: 10.1055/s-0028-1083203; Art ID: M03408SS © Georg Thieme Verlag Stuttgart · New York Abstract: D-Gulonic lactone or its L-isomer is easily converted to the vinyl lactone 1 via three convenient reactions in an overall 69% yield. Reaction of the D isomer of 1 with a variety of carbon, oxygen, sulfur, and nitrogen nucleophiles and a palladium catalyst produced carboxylic acids that were esterified with methyl iodide to give the esters 2. Alternatively, reaction of L-lactone 1 with Ph3P=CHCO2Et provided the Wittig product that underwent palladium-catalyzed rearrangement to give the cyclopentanone 3.
File Format	PDF HTM / HTML
Alternate Webpage(s)	http://www.xiuzhengrd.com/ejournals/pdf/synthesis/doi/10.1055/s-0028-1083203.pdf
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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