Universität zu Köln

Skrobo, Benedikt, Schloerer, Nils E., Neudoerfl, Joerg-M. and Deska, Jan ORCID: 0000-0003-4622-2365 (2018). Kirmse-Doyle- and Stevens-Type Rearrangements of Glutarate-Derived Oxonium Ylides. Chem.-Eur. J., 24 (13). S. 3209 - 3218. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3765

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Abstract

A novel chemoenzymatic synthetic cascade enables the preparation of densely decorated tetrahydrofuran building blocks. Here, the lipase-catalyzed desymmetrization of 3-alkoxyglutarates renders highly enantioenriched carboxylic acid intermediates, whose subsequent activation and oxonium ylide rearrangement by means of rhodium or copper complexes furnishes functionalized O-heterocycles with excellent diastereoselectivity. The two-step protocol offers a streamlined and flexible synthesis of tetrahydrofuranones bearing different benzylic, allylic or allenylic side chains with full control over multiple stereogenic centers.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Skrobo, Benedikt UNSPECIFIED UNSPECIFIED UNSPECIFIED Schloerer, Nils E. UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Deska, Jan UNSPECIFIED orcid.org/0000-0003-4622-2365 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-193055
DOI:	10.1002/chem.201704624
Journal or Publication Title:	Chem.-Eur. J.
Volume:	24
Number:	13
Page Range:	S. 3209 - 3218
Date:	2018
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1521-3765
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language ENANTIOSELECTIVE TOTAL-SYNTHESIS; SIGMATROPIC REARRANGEMENT; IODONIUM YLIDES; DESYMMETRIZATION; DIAZOMETHANE; GENERATION; ETHERS; TETRAHYDROFURAN-3-ONES; CARBOXYLATES; CYCLIZATION Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/19305