1992
DOI: 10.1039/c39920000759
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Novel carbocyclization of a D-glucose-derived alkene

Abstract: Cyclopentadiene reacts with a D-glucose-derived hex-3-enose derivative to give norbornene derivatives attached at the 2,3-position of a 1,6-anhydrohexose skeleton; although the bicyclic enone isolevoglucosenone is a plausible intermediate in this reaction, the products actually appear to arise through initial cycloaddition to a rearranged acyclic sugar derivative with subsequent generation of the anhydro ring.' 2+3 +4+5

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Cited by 30 publications
(38 citation statements)
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“…A broad range of catalysts based on Pd,12 Ru,13 Rh,14 Ni,15 Ir,16 Fe,17 Au,18 Co,19 Os,20 Ti,21 Zr,22 Re,23 Y,24 Sc,25 Hf,26 Cr,27 lanthanides,28 actinides,29 or main group elements30 can promote alkyne dimerization, albeit with different grades of success with regard to selectivity. In particular, preferential preparation of head‐to‐tail enynes has been disclosed for aromatic13i, 14e, 16b, 24a or aliphatic12d, 14a,c,g,k, 22a, 24c, 26, 29b alkynes, although examples of selective initiators regardless of the substituent on the alkyne are limited to the catalysts of Nakamura (Ti),21a Trost (Pd),12b Eisen (Al),30b and Zhang (Au)18 and their respective co‐workers.…”
Section: Introductionmentioning
confidence: 99%
“…A broad range of catalysts based on Pd,12 Ru,13 Rh,14 Ni,15 Ir,16 Fe,17 Au,18 Co,19 Os,20 Ti,21 Zr,22 Re,23 Y,24 Sc,25 Hf,26 Cr,27 lanthanides,28 actinides,29 or main group elements30 can promote alkyne dimerization, albeit with different grades of success with regard to selectivity. In particular, preferential preparation of head‐to‐tail enynes has been disclosed for aromatic13i, 14e, 16b, 24a or aliphatic12d, 14a,c,g,k, 22a, 24c, 26, 29b alkynes, although examples of selective initiators regardless of the substituent on the alkyne are limited to the catalysts of Nakamura (Ti),21a Trost (Pd),12b Eisen (Al),30b and Zhang (Au)18 and their respective co‐workers.…”
Section: Introductionmentioning
confidence: 99%
“…We then turned our attention to less polar solvents such as CHCl 3 (À12% de), AcOEt (À22% de) and toluene (À59% de) and observed inversion of the sense offacial selectivity, as reported earlier for another analogue of (À)-1a. 12 We thus could reach up to 70% de in favor of diastereoisomer (2S,3S)-2f in hexane by working under 0.0005 M high dilution conditions owing to the low solubility of dienophile (À)-1f, albeit with incomplete chemical conversion. Since the diastereoselectivity observed in the apolar Et 3 N (À45% de) was not as high as expected, we then turned our attention towards a Scheme 1 Figure 1.…”
Section: Resultsmentioning
confidence: 99%
“…Previously reported catalytic syntheses of enynes with other group 4 systems give mixtures of products, with the head-to-tail isomers being preferred (Scheme 1, A). [11][12][13] Here we disclose an easily accessed zirconium precatalyst which furnishes exclusively Z-enynes (B) in excellent yield. Stoichiometric organometallic investigations have resulted in the isolation of a catalytically competent bridged-amido-imido dimer, suggesting that such dinuclear species may account for the previously unobserved regio-and stereoselectivities reported here.…”
mentioning
confidence: 92%
“…4 One of the most convenient routes for preparing such enynes is the dimerization of two terminal alkynes (Scheme 1). This reaction is atom-economic and can be catalyzed by rare-earth metals, [5][6][7] actinides 8 and early [9][10][11][12][13] and late 14,15 transition metals. However, in many cases these reactions suffer from a lack of regioor stereoselectivity, which limits their synthetic utility.…”
mentioning
confidence: 99%
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