Universität zu Köln

Harnying, Wacharee, Neudoerfl, Joerg-M. and Berkessel, Albrecht ORCID: 0000-0003-0470-7428 (2020). Enantiospecific Synthesis of Nepetalactones by One-Step Oxidative NHC Catalysis. Org. Lett., 22 (2). S. 386 - 391. WASHINGTON: AMER CHEMICAL SOC. ISSN 1523-7052

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Abstract

An efficient oxidative NHC-catalyzed one-step transformation of (S)- or (R)-8-oxocitronellal to nepetalactone (NL) in enantio- and diastereomerically pure form has been developed. Several new and easy to make N-Mes- or N-Dipp-substituted 1,2,4-triazolium salts carrying nitroaromatic groups on N1 were synthesized and evaluated as precatalysts in combination with base and stoichiometric organic oxidant. Under optimized conditions, NLs are accessible in very good yields and diastereomerically pure under mild conditions. The oxidant used could be recovered and recycled under operationally simple conditions.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Harnying, Wacharee UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Berkessel, Albrecht UNSPECIFIED orcid.org/0000-0003-0470-7428 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-348631
DOI:	10.1021/acs.orglett.9b04034
Journal or Publication Title:	Org. Lett.
Volume:	22
Number:	2
Page Range:	S. 386 - 391
Date:	2020
Publisher:	AMER CHEMICAL SOC
Place of Publication:	WASHINGTON
ISSN:	1523-7052
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 N-HETEROCYCLIC CARBENES; THIAMINE ACTION; UMPOLUNG; DIASTEREOMERS; REACTIVITY; CHEMISTRY; MECHANISM; ALDEHYDES; ALCOHOLS; CATNIP Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/34863