Universität zu Köln

Hemmersbach, Lars, Romanski, Steffen, Botov, Svetlana, Adler, Andreas, Neudoerfl, Joerg-Martin and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2021). On the Diastereoselectivity of the Complexation of Ketopinic Acid-Derived 2-Acyloxy-1,3-cyclohexadienes and the Configurational Stability of Dienol-Fe(CO)(3) Complexes. A Case Study. Organometallics, 40 (16). S. 2909 - 2915. WASHINGTON: AMER CHEMICAL SOC. ISSN 1520-6041

Full text not available from this repository.

Abstract

In the course of an attempt to synthesize 2-acyloxycyclohexa-1,3-diene-Fe (CO)(3) complexes in nonracemic form, we reinvestigated the fully diastereoselective Fe(CO)(3) complexation of (S,S)-2-ketopinoyloxy-1,3-cyclohexadiene, which had been described by Yeh and co-workers (Organometallics 2001, 20, 289-295). However, after cleaving off the chiral auxiliary unit, we only obtained racemic complexes, also for a related substrate. For this reason, we performed control experiments to exclude possible racemization mechanisms and confirmed the configurational integrity of the dienol-Fe(CO)(3) intermediates using stereochemically defined dihydrocarvone-derived complexes. We finally could show that the complexation described by Yeh actually proceeds without any detectable diastereoselectivity. At the end, the virtually inseparable diastereomers of the chiral complexation products could be distinguished by careful NMR and chiral HPLC analyses.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Hemmersbach, Lars UNSPECIFIED UNSPECIFIED UNSPECIFIED Romanski, Steffen UNSPECIFIED UNSPECIFIED UNSPECIFIED Botov, Svetlana UNSPECIFIED UNSPECIFIED UNSPECIFIED Adler, Andreas 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:38-561383
DOI:	10.1021/acs.organomet.1c00354
Journal or Publication Title:	Organometallics
Volume:	40
Number:	16
Page Range:	S. 2909 - 2915
Date:	2021
Publisher:	AMER CHEMICAL SOC
Place of Publication:	WASHINGTON
ISSN:	1520-6041
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language IRON TRICARBONYL COMPLEXES; ASYMMETRIC-SYNTHESIS; NUCLEOSIDE ANALOGS; ESTER; CORMS Multiple languages Chemistry, Inorganic & Nuclear; Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/56138