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:
CreatorsEmailORCIDORCID Put Code
Nguyen, Xuan B.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Nakano, YujiUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Duggan, Nishariithi M.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Scott, LydiaUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Breugst, MartinUNSPECIFIEDorcid.org/0000-0003-0950-8858UNSPECIFIED
Lupton, David W.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
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: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
TO-TAIL DIMERIZATION; BOND-FORMING REACTIONS; STEREOSELECTIVE-SYNTHESIS; CONJUGATE-ADDITION; HOMOALDOL REACTION; ALPHA,BETA-UNSATURATED ALDEHYDES; LEWIS BASICITY; UMPOLUNG; CYCLOPROPANOLS; OLEFINATIONMultiple languages
Chemistry, MultidisciplinaryMultiple languages
Refereed: Yes
URI: http://kups.ub.uni-koeln.de/id/eprint/14444

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