Universität zu Köln

Nguyen, Xuan B., Nakano, Yuji, Duggan, Nishariithi M., Scott, Lydia, Breugst, Martin ORCID: 0000-0003-0950-8858 and Lupton, David W. (2019). N-Heterocyclic Carbene Catalyzed (5+1) Annulations Exploiting a Vinyl Dianion Synthon Strategy. Angew. Chem.-Int. Edit., 58 (33). S. 11483 - 11491. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3773

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Abstract

Direct polarity inversion of conjugate acceptors provides a valuable entry to homoenolates. N-heterocyclic carbene (NHC) catalyzed reactions, in which beta-unsubstituted conjugate acceptors undergo homoenolate formation and C-C bond formation twice, have been developed. Specifically, the all-carbon (5+1) annulations give a range of mono- and bicyclic cyclohexanones (31 examples). In the first family of annulations, beta-unsubstituted acrylates tethered to a divinyl ketone undergo cycloisomerization, providing hexahydroindenes and tetralins. In the second, partially untethered substrates undergo an intermolecular (5+1) annulation involving dimerization followed by cycloisomerization. While enantioselectivity was not possible with the former, the latter proved viable, allowing cyclohexanones to be produced with high levels of enantiopurity (most >95:5 e.r.) and exclusive diastereoselectivity (>20:1 d.r.). Derivatizations and mechanistic studies are also reported.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Nguyen, Xuan B. UNSPECIFIED UNSPECIFIED UNSPECIFIED Nakano, Yuji UNSPECIFIED UNSPECIFIED UNSPECIFIED Duggan, Nishariithi M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Scott, Lydia UNSPECIFIED UNSPECIFIED UNSPECIFIED Breugst, Martin UNSPECIFIED orcid.org/0000-0003-0950-8858 UNSPECIFIED Lupton, David W. UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-144445
DOI:	10.1002/anie.201905475
Journal or Publication Title:	Angew. Chem.-Int. Edit.
Volume:	58
Number:	33
Page Range:	S. 11483 - 11491
Date:	2019
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1521-3773
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 TO-TAIL DIMERIZATION; BOND-FORMING REACTIONS; STEREOSELECTIVE-SYNTHESIS; CONJUGATE-ADDITION; HOMOALDOL REACTION; ALPHA,BETA-UNSATURATED ALDEHYDES; LEWIS BASICITY; UMPOLUNG; CYCLOPROPANOLS; OLEFINATION Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/14444