Du, Qingwei, Neudoerfl, Joerg-Martin and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2018). Chiral Phosphine-Phosphite Ligands in Asymmetric Gold Catalysis: Highly Enantioselective Synthesis of Furo[3,4-d]-Tetrahydropyridazine Derivatives through [3+3]-Cycloaddition. Chem.-Eur. J., 24 (10). S. 2379 - 2384. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3765

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Abstract

The Au-I-catalyzed reaction of 2-(1-alkynyl)-2-alken-1-ones with azomethine imines regio- and diastereoselectively affords furo[3,4-d]tetrahydropyridazines in a tandem cyclization/intermolecular [3+3]-cycloaddition process under mild conditions. By employing a chiral gold catalyst (prepared in situ from a Taddol-derived phosphine-phosphite ligand, Me2SAuCl, and AgOTf) high yields and enantioselectivities (up to 94% yield, up to 96%ee) are obtained. The method provides an efficient modular route to substituted heterotricyclic furan derivatives and can be easily scaled up (using catalyst loads of only 0.15 mol%).

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Du, QingweiUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Neudoerfl, Joerg-MartinUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Schmalz, Hans-GuentherUNSPECIFIEDorcid.org/0000-0003-0489-1827UNSPECIFIED
URN: urn:nbn:de:hbz:38-195889
DOI: 10.1002/chem.201800042
Journal or Publication Title: Chem.-Eur. J.
Volume: 24
Number: 10
Page Range: S. 2379 - 2384
Date: 2018
Publisher: WILEY-V C H VERLAG GMBH
Place of Publication: WEINHEIM
ISSN: 1521-3765
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
AZOMETHINE IMINES; 1,3-DIPOLAR CYCLOADDITION; PYRIDAZINE DERIVATIVES; ANTIMICROBIAL ACTIVITY; BIOLOGICAL-ACTIVITY; GRIGNARD-REAGENTS; N-ALLENAMIDES; FURAN RINGS; 2-(1-ALKYNYL)-2-ALKEN-1-ONES; INHIBITORSMultiple languages
Chemistry, MultidisciplinaryMultiple languages
Refereed: Yes
URI: http://kups.ub.uni-koeln.de/id/eprint/19588

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