1997
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Abstract: Density functional calculations (Becke3LYP/6-31G(d)) on the (3 + 2) transition structures of osmium tetroxide mediated dihydroxylations of chiral allylic ethers show that the stereoselectivity is controlled by the “inside alkoxy effect” (Stork/Houk-Jäger model). In the special case of Z-disubstituted alkenes, 1,3-allylic strain (Kishi model) controls the stereoselectivity.

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“…[283] This apparently general trend is in agreement with the Stork-Houk-Jäger "inside-alkoxy" model. [284][285][286] The examination of substrates that contain 1,2-disubstituted cyclopropanes revealed several interesting trends. For example, treatment of the 1,2-cis-disubstituted cyclopropane 425 with the Ru catalyst under standard conditions produced exclusively the diastereomer 426 [Eq.…”
Section: Ruthenium-catalyzed [5+2] Cycloadditionmentioning
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rupbmjkragerfmgwileyiopcupepmcmbcthiemesagefrontiersapsiucrarxivemeralduhksmucshluniversity-of-gavle
“…[283] This apparently general trend is in agreement with the Stork-Houk-Jäger "inside-alkoxy" model. [284][285][286] The examination of substrates that contain 1,2-disubstituted cyclopropanes revealed several interesting trends. For example, treatment of the 1,2-cis-disubstituted cyclopropane 425 with the Ru catalyst under standard conditions produced exclusively the diastereomer 426 [Eq.…”
Section: Ruthenium-catalyzed [5+2] Cycloadditionmentioning
“…Other recent support for the [3+2] mechanism has come from available experimental data [15] and new measurements of kinetic isotope effects [14,16] . Several stereoselective reactions have also been reported by Corey [15] , Houk [17] , Sharpless [18] , Haller [19] , and coworkers. To our knowledge, there have been only a few reports that styrene was catalyzed by (DHQD) 2 PYDZ·OsO 4 through theoretical calculations [20,21] .…”
Section: Introductionmentioning
“…[284][285][286] Untersuchungen mit Substraten, die 1,2-disubstituierte Cyclopropane enthalten, zeigten mehrere interessante Trends: Unter Standardbedingungen lieferte die Behandlung des 1,2-cis-disubstituierten Cyclopropans 425 mit dem Ruthenium-Katalysator auschließlich das Diastereomer 426 [Gl. (95)].…”
Section: B M Trost Et Alunclassified