2004
DOI: 10.1021/jo0487810
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Highly Enantioselective Conjugate Additions of Potassium Organotrifluoroborates to Enones by Use of Monodentate Phosphoramidite Ligands

Abstract: The use of phosphoramidite ligands in the rhodium-catalyzed asymmetric conjugate addition of potassium organotrifluoroborates to various enones in the absence of water is described. A systematic search for effective catalysts has been performed by use of high-throughput screening methods. Initially, we have screened reaction conditions, catalyst precursors, and focused ligand libraries. In the next stage we have used the monodentate ligand combination approach, and finally we have made a library of 96 differen… Show more

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Cited by 121 publications
(43 citation statements)
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“…A mixed ligand approach has been employed in rhodium [17,25,28,29] and iridium-catalyzed [7] asymmetric hydrogenations and in rhodium-catalyzed additions of boronic acids. [22] It is also possible to use mixed complexes based on a monodentate chiral ligand and a non-chiral phosphorus ligand. [17,26] The fact that the structure of monodentate ligands can be varied easily enables us to screen a very large number of different complexes in the asymmetric hydrogenation.…”
Section: Resultsmentioning
confidence: 99%
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“…A mixed ligand approach has been employed in rhodium [17,25,28,29] and iridium-catalyzed [7] asymmetric hydrogenations and in rhodium-catalyzed additions of boronic acids. [22] It is also possible to use mixed complexes based on a monodentate chiral ligand and a non-chiral phosphorus ligand. [17,26] The fact that the structure of monodentate ligands can be varied easily enables us to screen a very large number of different complexes in the asymmetric hydrogenation.…”
Section: Resultsmentioning
confidence: 99%
“…[13] In addition, they are amenable to parallel synthesis. [14] We have developed the use of monodentate phosphoramidites as ligands for asymmetric hydrogena-tion, [15][16][17] conjugate addition [18] , allylic alkylation, [19] asymmetric arylation of aldehydes, [20] ketones [21,22] and substituted imines. [23] Herein we report the first asymmetric hydrogenation of quinolines catalyzed by iridium complexes based on monodentate BINOL-derived phosphoramidites.…”
Section: Introductionmentioning
confidence: 99%
“…The known chiral phosphoramidite ligands of the type 1a-d and 2a shown in Figure 1 were synthesized according to literature procedures. [1,7] Similarly, the new ligand 2b was synthesized as outlined in Eq. (1).…”
Section: Synthesis Of Novel Half-sandwich Rutheniumphosphoramidite Comentioning
confidence: 99%
“…[2] Typically phosphoramidites are utilized in situ in combination with a metal complex precursor to yield efficient catalyst systems for such conversions as enantioselective conjugate enone addition reac- [2a,g,3] hydrogenations, [4] allylic alkylations, [5] hydrosilylations, [6] vinylations, [7] cycloadditions, [8] Diels- Alder [9] and Heck reactions. [10] The nature of the catalytically active species for these in situ catalyst systems is not always known.…”
Section: Introductionmentioning
confidence: 99%
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