Direct Catalytic Asymmetric Three-Component Kabachnik–Fields Reaction†
Xu Cheng Dr.
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2999
Search for more papers by this authorRichard Goddard Dr.
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2999
Search for more papers by this authorGernot Buth Dr.
ISS, Forschungszentrum Karlsruhe, Postfach 3640, 76021 Karlsruhe (Germany)
Search for more papers by this authorBenjamin List Prof. Dr.
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2999
Search for more papers by this authorXu Cheng Dr.
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2999
Search for more papers by this authorRichard Goddard Dr.
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2999
Search for more papers by this authorGernot Buth Dr.
ISS, Forschungszentrum Karlsruhe, Postfach 3640, 76021 Karlsruhe (Germany)
Search for more papers by this authorBenjamin List Prof. Dr.
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2999
Search for more papers by this authorWe thank Alfred Deege and Heike Hinrichs for HPLC measurements. This work was funded in part by the DFG (priority program “Organocatalysis” SPP1179). Generous support by the Max Planck Society, Novartis (Young Investigator Award to B.L.), the Fonds der Chemischen Industrie (Silver Award to B.L.), and AstraZeneca (Research Award in Organic Chemistry to B.L.) is gratefully acknowledged.
Graphical Abstract
As mimics of α-amino acids, α-amino phosphonates have great promise as antibacterial and anti-HIV agents as well as protease inhibitors. Racemic α-branched aldehydes react, in the presence the new chiral phosphoric acid catalyst 1, directly with p-anisidine (PMPNH2) and a phosphite to furnish β-branched α-amino phosphonates highly diastereoselectively and enantioselectively. Anth=anthracenyl.
Supporting Information
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- 17Alternative nitrogen sources that have been investigated include BocNH2, CbzNH2, benzamide, benzylamine, dibenzylamine, morpholine, and diphenylamine, which all gave no reaction. Among the anilines tested, p-anisidine gave higher enantioselectivities than p-hydroxylaniline, p-ethoxyaniline, p-phenoxyaniline, and o-methoxyaniline. We have also investigated other phospites, including diethyl-, diisopropyl-, and di(o-nitrobenzyl)phosphite and found di(3-pentyl)phosphite gave the highest enantioselectivities.
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- 19For synthetic details, see the Supporting Information.
- 20CCDC-679478 (λ=1.54178 Å) and CCDC-679479 (λ=1.77121 Å) (4 g) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
