2014
DOI: 10.1021/ja501568k
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Immobilized Bisdiazaphospholane Catalysts for Asymmetric Hydroformylation

Abstract: Condensation reactions of enantiopure bis-3,4-diazaphospholanes (BDPs) that are functionalized with carboxylic acids enable covalent attachment to bead and silica supports. Exposure of tethered BDPs to the hydroformylation catalyst precursor, Rh(acac)(CO)2, yields catalysts for immobilized asymmetric hydroformylation (iAHF) of prochiral alkenes. Compared with homogeneous catalysts, catalysts immobilized on Tentagel resins exhibit similarly high regioselectivity and enantioselectivity. When corrected for appare… Show more

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Cited by 67 publications
(21 citation statements)
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“…Another entry point is the production of 3-aryl-1-butene following RajanBabushydrovinylation process of styrenes 24 (C). [35] The last approach (E)isbased on adynamic kinetic resolution of aldehyde 26 and subsequent reduction. [34] Landis has pioneered highly effective enantioselective hydroformylation processes that in the reaction of 24 would be expected to furnish an aldehyde,w hich following reduction would afford 21.…”
Section: Deracemizing Reductase Activitymentioning
confidence: 99%
“…Another entry point is the production of 3-aryl-1-butene following RajanBabushydrovinylation process of styrenes 24 (C). [35] The last approach (E)isbased on adynamic kinetic resolution of aldehyde 26 and subsequent reduction. [34] Landis has pioneered highly effective enantioselective hydroformylation processes that in the reaction of 24 would be expected to furnish an aldehyde,w hich following reduction would afford 21.…”
Section: Deracemizing Reductase Activitymentioning
confidence: 99%
“…Hence, there is ag rowingi nterest to develop more economic technologies, which allow for quantitativec atalyst recycling. [6] In this respect, many research groups investigated both heterogeneous and immobilised homogeneous catalysts for the title reaction, mainly using rhodium, [7][8][9][10][11][12][13][14] but also cobalt systems [15][16][17] as well as otherm etals. [18][19][20][21][22][23] The main problem of all these catalysts is the leachingo fa ctive metal speciesf rom the support in the presence of CO.…”
Section: Introductionmentioning
confidence: 99%
“…Enantioselective hydroformylation : The immobilization of asymmetric hydroformylation (AHF) catalysts is very expensive, and there are very few reports for their preparation. Landis′ group reported a complete analysis of immobilized AHF catalysts . The AHF catalysts 57 were formed from the activated tetraacyl fluoride bis‐3,4‐diazaphospholanes (BDP), Tentagel‐S‐NH 2 resins, and Rh(acac)(CO) 2 (Scheme ).…”
Section: Heterogeneous Enantioselective Catalysis In Flowmentioning
confidence: 99%