Universität zu Köln

Eitzinger, Andreas ORCID: 0000-0002-3231-9716, Otevrel, Jan ORCID: 0000-0002-8275-4177, Haider, Victoria, Macchia, Antonio, Massa, Antonio, Faust, Kirill, Spingler, Bernhard ORCID: 0000-0003-3402-2016, Berkessel, Albrecht and Waser, Mario ORCID: 0000-0002-8421-8642 (2021). Enantioselective Bifunctional Ammonium Salt-Catalyzed Syntheses of 3-CF3S-, 3-RS-, and 3-F-Substituted Isoindolinones. Adv. Synth. Catal., 363 (7). S. 1955 - 1963. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1615-4169

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Abstract

We herein report the ammonium salt-catalyzed synthesis of chiral 3,3-disubstituted isoindolinones bearing a heteroatom functionality in the 3-position. A broad variety of differently substituted CF3S- and RS-derivatives were obtained with often high enantioselectivities when using Maruoka's bifunctional chiral ammonium salt catalyst. In addition, a first proof-of-concept for the racemic synthesis of the analogous F-containing products was obtained as well, giving access to one of the rare examples of a fairly stable alpha-F-alpha-amino acid derivative.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Eitzinger, Andreas UNSPECIFIED orcid.org/0000-0002-3231-9716 UNSPECIFIED Otevrel, Jan UNSPECIFIED orcid.org/0000-0002-8275-4177 UNSPECIFIED Haider, Victoria UNSPECIFIED UNSPECIFIED UNSPECIFIED Macchia, Antonio UNSPECIFIED UNSPECIFIED UNSPECIFIED Massa, Antonio UNSPECIFIED UNSPECIFIED UNSPECIFIED Faust, Kirill UNSPECIFIED UNSPECIFIED UNSPECIFIED Spingler, Bernhard UNSPECIFIED orcid.org/0000-0003-3402-2016 UNSPECIFIED Berkessel, Albrecht UNSPECIFIED UNSPECIFIED UNSPECIFIED Waser, Mario UNSPECIFIED orcid.org/0000-0002-8421-8642 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-590438
DOI:	10.1002/adsc.202100029
Journal or Publication Title:	Adv. Synth. Catal.
Volume:	363
Number:	7
Page Range:	S. 1955 - 1963
Date:	2021
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1615-4169
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language Chemistry, Applied; Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/59043