2007
DOI: 10.1002/anie.200700533
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Mixtures of Chiral Phosphorous Acid Diesters and Achiral P Ligands in the Enantio‐ and Diastereoselective Hydrogenation of Ketimines

Abstract: In this Communication, the structure of ligand 7 was incorrectly drawn. The correct structure is shown below.

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Cited by 106 publications
(33 citation statements)
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“…[2] Combinatorial chemistry approaches and high-throughput catalyst screenings have been demonstrated to be increasingly important. [3] Fort he generation of catalyst libraries based on chiral ligands,the use of supramolecular ligand building blocks that form bidentate ligands by self-assembly is apowerful strategy as the number of catalysts grows exponentially with the number of synthesized building blocks. [4] Next to interactions between the two ligand building blocks,hydrogen bonding between functional groups of the substrate and the ligands at the metal complex can contribute to catalyst selectivity.…”
mentioning
confidence: 99%
“…[2] Combinatorial chemistry approaches and high-throughput catalyst screenings have been demonstrated to be increasingly important. [3] Fort he generation of catalyst libraries based on chiral ligands,the use of supramolecular ligand building blocks that form bidentate ligands by self-assembly is apowerful strategy as the number of catalysts grows exponentially with the number of synthesized building blocks. [4] Next to interactions between the two ligand building blocks,hydrogen bonding between functional groups of the substrate and the ligands at the metal complex can contribute to catalyst selectivity.…”
mentioning
confidence: 99%
“…Thus, up to 83% ee was achieved when the hinder tBusubstituted SPO was applied in the hydrogenation of N-benzylimines in the presence of additional pyridine as the additive (Scheme 30). The application of structurally similar and strategically related chiral phosphoric acid together with achiral phosphines or phosphites in the asymmetric hydrogenation of N-benzylimines were reported by Reetz et al, achieving excellent enantioselectivities (up to 92% ee) [86]. …”
Section: Other Ir Catalystsmentioning
confidence: 98%
“…3 The role of achiral ligands in enhancing the reactivity and selectivity in asymmetric reactions has been investigated by several groups in recent years. 3,[5][6][7][8][9][10][11][12][13] Thus, catalysis by metal-ligand complexes containing both achiral and chiral ligands has been reported in the asymmetric alkylation of aldehydes, 5 hydrogenation of imines 6 and olefins, 7 hydroformylation 8 and addition of organozinc reagents to α-keto esters. 9 However, reports on the reversal of enantioselectivity by achiral ligands are limited to metalligand catalyzed boronic acid addition to activated olefins, 10 olefin hydrogenation, 11 dialkylzinc addition to aldehyde 12 and Diels-Alder reactions.…”
Section: Introductionmentioning
confidence: 99%
“…Other additives such as ethylenediamine A3, ethylene glycol A4 and 12-crown-4 A5 provided improved yields without affecting the stereoselectivity (Table 1, entries [4][5][6]. Surprisingly, the addition of NMM A6 to the precatalyst, i.e.…”
mentioning
confidence: 99%