2006
DOI: 10.1021/ja067073o
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Copper-Catalyzed Rearrangement of Vinyl Oxiranes

Abstract: A novel copper-catalyzed vinyl oxirane ring expansion protocol has been developed. A wide range of vinyl oxiranes can be rearranged to 2,5-dihydrofurans in excellent yields in the presence of electrophilic copper(II) acetylacetonate catalysts. Regioisomeric vinyl oxiranes can be converted to a single dihydrofuran product using these conditions. This method uses low catalyst loadings (0.5-5 mol %), has good tolerance of substitution patterns, and can be done in the absence of solvent.

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Cited by 78 publications
(49 citation statements)
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“…Based on previous work by our group on the catalytic ring expansion of vinyl oxiranes and vinyl thiiranes,16 copper catalysts were tested (Table 1). The more electrophilic copper(II) hexafluoroacetylacetonate (entries 14-18) proved far superior to other commercially available and synthetic catalysts.…”
mentioning
confidence: 99%
“…Based on previous work by our group on the catalytic ring expansion of vinyl oxiranes and vinyl thiiranes,16 copper catalysts were tested (Table 1). The more electrophilic copper(II) hexafluoroacetylacetonate (entries 14-18) proved far superior to other commercially available and synthetic catalysts.…”
mentioning
confidence: 99%
“…Thus, as shown in Scheme , ring opening of oxirane ( S )‐ 18 with lithium acetylide–EDA gave homopropargylic alcohol ( S )‐ 19 in 70 % yield. 1‐Nonen‐3‐one ( 21 ), needed to complete the carbon skeleton present in (–)‐ 2 , was obtained in 90 % yield after oxidation of commercially available 1‐nonen‐3‐ol ( 20 ) with Jones reagent, as described in the literature 13. Rh‐catalyzed conjugate addition of terminal alkyne ( S )‐ 19 to enone 21 afforded enantiopure ( S )‐ 22 in 94 % yield, after chromatographic purification.…”
Section: Resultsmentioning
confidence: 99%
“…Following cross metathesis between thiophosphate enone and a terminal alkene, a vinyl thiirane was accessed by treating the product with sodium borohydride. Njardarson's copper-catalyzed ring expansion protocol [25] then converted the vinyl thiirane into a 2,5-dihydrothiophene. Careful chemo-and substrate controlled dihydroxylation of the double bond afforded the diol shown, which is an intermediate in Ohrui's [26] biotin synthesis.…”
Section: Thiiranementioning
confidence: 99%