Universität zu Köln

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:	Creators Email ORCID ORCID Put Code Du, Qingwei UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-Martin UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED
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:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language 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; INHIBITORS Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/19588