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Indium-mediated allylation of aldehydes, ketones and sulfonimines with 2-(alkoxy)allyl bromides

โœ Scribed by Heemal Dhanjee; Thomas G. Minehan

Book ID
104098238
Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
843 KB
Volume
51
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

a b s t r a c t 2-(Alkoxy)propenyl bromides are readily prepared from 1,3-dibromo-2-propanol in a two-step sequence involving hydroxyl protection and sodium hydride-induced dehydrobromination. Indium-mediated allylation of aldehydes, ketones, and sulfonimines with 2-(alkoxy)propenyl bromides furnishes the corresponding homoallylic alcohols and sulfonamines in good yields. The products can be easily transformed into b-hydroxy ketones and esters, as well as substituted dihydropyrans, and protected bamino acids. Chiral 2-(alkoxy)propenyl halides, derived from (ร€)-menthol and D-glucal, furnish diastereomerically enriched products.

๐Ÿ“œ SIMILAR VOLUMES

Indium-mediated allylation of carbonyl c
Indium-mediated allylation of carbonyl compounds with an allylic bromide in aqueous media: anomalous syn-diastereoselectivity regardless of allylic bromide geometry
โœ Teck-Peng Loh; Zheng Yin; Hong-Yan Song; Kee-Leng Tan ๐Ÿ“‚ Article ๐Ÿ“… 2003 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 315 KB

Anomalous syn-diastereoselectivity of indium-mediated coupling of aldehydes with bromides Z-3b and E-3b is reported. The reaction afforded high syn selectivity regardless of the allylic bromide geometry. Preliminary studies on the enantioselective indium-mediated allylation were attempted and found