2006
DOI: 10.1002/adsc.200505463
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Homo‐ and Cross‐Olefin Metathesis Coupling of Vinylphosphane Oxides and Electron‐Poor Alkenes: Access to P‐Stereogenic Dienophiles

Abstract: Vinylphosphane oxides 6 undergo catalytic olefin homo-metathesis leading to achiral and P-stereogenic diphosphane dioxides 7 with exclusive (E)-selectivity. Similarly, EWG-substituted vinylphosphane oxides 11, 12 could be prepared with complete (E)-olefin selectivity via olefin cross-metathesis with electron-deficient substrates, such as methyl acrylate and 2-fluorostyrene, using nitro-Hoveyda ruthenium precatalyst III. Cross-and homo-metathesis of chiral non-racemic vinylphosphane oxides proceeds without race… Show more

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Cited by 51 publications
(26 citation statements)
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“…[29] Gouvernour and Grela have simultaneously reported a successful CM of vinyl phosphine partners catalysed by Gru-II. [30] However, while the latter initiator was found to be ineffective in the more challenging self-CM of vinyl phosphane oxides, [31] this transformation was accomplished with the phosphane-free complex Gre-II. [31] Contrary to some previous reports, [32] we have discovered that CM of vinyl sulfones can also be effectively Scheme 4.…”
Section: Straightforward Enyne Cycloisomerisationmentioning
confidence: 99%
“…[29] Gouvernour and Grela have simultaneously reported a successful CM of vinyl phosphine partners catalysed by Gru-II. [30] However, while the latter initiator was found to be ineffective in the more challenging self-CM of vinyl phosphane oxides, [31] this transformation was accomplished with the phosphane-free complex Gre-II. [31] Contrary to some previous reports, [32] we have discovered that CM of vinyl sulfones can also be effectively Scheme 4.…”
Section: Straightforward Enyne Cycloisomerisationmentioning
confidence: 99%
“…However, these methods suffer from lack of stereoselectivity, limited substrate scope and the use of relatively drastic conditions that were not compatible with sensitive functional groups etc. 74 Hence, decarboxylative C-P bond formation can address an efficient alternative protocol to overcome these drawbacks. Cinnamic acids and alkyne acids were subjected to decarboxylative C-P bond formation for the first time.…”
Section: C-p Bond Formationmentioning
confidence: 99%
“…The behavior of differently substituted acrylates as substrates for the cross‐metathesis with ethyl sorbate showed the same correlations that were reported previously . A larger carboxylic group substituent decreased the reaction rate of the metathesis by making it more difficult for the molecules to reach the Ru active site . As seen in Table , the smaller the substituent of the acrylate, the higher the conversion to the cross‐metathesis product.…”
Section: Resultsmentioning
confidence: 99%
“…[48] Al arger carboxylic group substituent de-creasedt he reaction rate of the metathesis by making it more difficult for the molecules to reacht he Ru active site. [49] As seen in Table 3, the smaller the substituent of the acrylate, the higher the conversion to the cross-metathesis product. Moreover,u pon using fumarate as ar eactant ( Table 3, entry 5), the reactivity for cross-metathesisw as furtherd iminished owing to steric hindrance and the highstability of the diester.…”
Section: Reactantsubstituent Effectsmentioning
confidence: 99%