Universität zu Köln

Marques, Carolina Silva, Dindaroglu, Mehmet, Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 and Burke, Anthony J. (2014). Asymmetric catalytic arylation of ethyl glyoxylate using organoboron reagents and Rh(I)-phosphane and phosphane-phosphite catalysts. RSC Adv., 4 (12). S. 6035 - 6042. CAMBRIDGE: ROYAL SOC CHEMISTRY. ISSN 2046-2069

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Abstract

Herein we report the first application of Rh(I)-phosphane and phosphane-phosphite catalysts in the enantioselective catalytic arylation of ethyl glyoxylate with organoboron reagents, providing access to ethyl mandelate derivatives in high yield (up to 99%) and moderate to very good enantioselectivities (up to 75% ee). Commercial phosphane ligands, such as (R)-MonoPhos and (R)-Phanephos were tested, as well as non-commercial (R, R)-TADDOL-derived phosphane-phosphite ligands. Those ligands containing bulky substituents in the ortho-and para-positions of the chiral phosphite moiety were found to be the most selective.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Marques, Carolina Silva UNSPECIFIED UNSPECIFIED UNSPECIFIED Dindaroglu, Mehmet UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED Burke, Anthony J. UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-452716
DOI:	10.1039/c3ra47000h
Journal or Publication Title:	RSC Adv.
Volume:	4
Number:	12
Page Range:	S. 6035 - 6042
Date:	2014
Publisher:	ROYAL SOC CHEMISTRY
Place of Publication:	CAMBRIDGE
ISSN:	2046-2069
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 ARYLBORONIC ACIDS; CONJUGATE ADDITION; ENANTIOSELECTIVE 1,4-ADDITION; GRIGNARD-REAGENTS; COUPLING REACTION; LIGANDS; DERIVATIVES; PERFORMANCE; IMINES; ACCESS Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/45271