Universität zu Köln

Termath, Andreas Ole, Sebode, Hanna, Schlundt, Waldemar, Stemmler, Rene T., Netscher, Thomas, Bonrath, Werner and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2014). Total Synthesis of (R, R, R)-alpha-Tocopherol Through Asymmetric Cu-Catalyzed 1,4-Addition. Chem.-Eur. J., 20 (38). S. 12051 - 12056. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3765

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Abstract

By introducing a disposable activating substituent at C-3, the asymmetric 1,4-addition to a notoriously unreactive 2-substituted chromenone was achieved with high levels of (2R)-stereoselectivity in the presence of a chiral CuI-phosphoramidite complex as a catalyst. This paved the way for an efficient and conceptually novel synthesis of (R, R, R)-alpha-tocopherol from readily available starting materials.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Termath, Andreas Ole UNSPECIFIED UNSPECIFIED UNSPECIFIED Sebode, Hanna UNSPECIFIED UNSPECIFIED UNSPECIFIED Schlundt, Waldemar UNSPECIFIED UNSPECIFIED UNSPECIFIED Stemmler, Rene T. UNSPECIFIED UNSPECIFIED UNSPECIFIED Netscher, Thomas UNSPECIFIED UNSPECIFIED UNSPECIFIED Bonrath, Werner UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-428670
DOI:	10.1002/chem.201404379
Journal or Publication Title:	Chem.-Eur. J.
Volume:	20
Number:	38
Page Range:	S. 12051 - 12056
Date:	2014
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 PHOSPHINE-PHOSPHITE-LIGANDS; ALPHA-TOCOPHERYL ACETATE; CONJUGATE ADDITION; GRIGNARD-REAGENTS; VITAMIN-E; TRISUBSTITUTED ENONES; HYDROGENATION; BIOAVAILABILITY; STEREOISOMERS; CONSTRUCTION Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/42867