2003
DOI: 10.1021/jo030007+
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A Comparison of Monocyclic and Bicyclic Phospholanes as Acyl-Transfer Catalysts

Abstract: The synthesis and evaluation of chiral phosphines 11, 15a, 19a, 24a, and 28a as nucleophilic catalysts for anhydride activation and kinetic resolution of alcohols is described. The relative reactivity follows the order 11a > 11b > 15a > 1 in the monocyclic series, and 24a > 19a > 28ain the bicyclic series, with an overall rate advantage of ca. 2 orders of magnitude for the bicyclic phospholanes over the monocyclic analogues. The increased reactivity of the bicyclic phospholanes for the acylation of alcohols is… Show more

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Cited by 61 publications
(51 citation statements)
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References 24 publications
(25 reference statements)
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“…Several bicyclic phosphetanes abbreviated PBOs (2-phosphabicyclo[3.3.0]octane) were prepared by the group of Vedejs and applied as organocatalysts [19]. One approach started with cyclopentanone ester 1 which was reduced with LiAlH 4 to the diol 2 (Scheme 2.4).…”
Section: Asymmetric Monophosphetanesmentioning
confidence: 99%
See 1 more Smart Citation
“…Several bicyclic phosphetanes abbreviated PBOs (2-phosphabicyclo[3.3.0]octane) were prepared by the group of Vedejs and applied as organocatalysts [19]. One approach started with cyclopentanone ester 1 which was reduced with LiAlH 4 to the diol 2 (Scheme 2.4).…”
Section: Asymmetric Monophosphetanesmentioning
confidence: 99%
“…Numerous monocyclic and bicyclic phospholanes were prepared by the group of Vedejs as exemplarily shown in Scheme 3.12 [19,59]. The pathway illustrated in Scheme 3.13 provided access to phosphabicyclo[3.3.0]octanes (abbreviated as BPOs).…”
Section: Mono(phospholanes)mentioning
confidence: 99%
“…Although not detected, it has been postulated that alcohol acylations catalyzed by phosphabicyclooctane derivatives probably involve a P ‐acylphosphonium carboxylate intermediate and a tight ion‐pair transition state 39…”
Section: Phosphinesmentioning
confidence: 99%
“…Vedejs und Mitarbeiter nutzten die entsprechenden BH 3 -Phosphin-Komplexe als Katalysatorvorstufen; die freien Phosphine werden durch Erwärmen des Komplexes in Gegenwart von Pyrrolidin freigesetzt. [133,134,137,140,141] 2004 zeigten Vedejs und MacKay, dass sich auch die Tetrafluoroborsäuresalze dieser Katalysatoren eignen; In-situ-Deprotonierung mit Et 3 N setzt den Katalysator dann frei. [142] Mechanistische und Konformationsstudien [137] sowie parallele kinetische Racematspaltungen [143] wurden ebenfalls durchgeführt.…”
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“…[133,134,137,140,141] 2004 zeigten Vedejs und MacKay, dass sich auch die Tetrafluoroborsäuresalze dieser Katalysatoren eignen; In-situ-Deprotonierung mit Et 3 N setzt den Katalysator dann frei. [142] Mechanistische und Konformationsstudien [137] sowie parallele kinetische Racematspaltungen [143] wurden ebenfalls durchgeführt. [141] 2003 berichteten Fujimoto et al von der Synthese eines auf einem Cinchona-Alkaloid basierenden, chiralen Phosphinits 278.…”
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