+ Site Statistics
References:
54,258,434
Abstracts:
29,560,870
PMIDs:
28,072,757
+ Search Articles
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ PDF Full Text
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Translate
+ Recently Requested

N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate



N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate



Chemical Science 8(3): 1936-1941



The N-heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindole and enals was developed, giving the corresponding spirocyclic oxindole-γ-lactones in good yields with high to excellent diastereo- and enantioselectivities. The challenging aliphatic enals worked effectively using this strategy. The oxidative cross coupling of homoenolate and enolate via single electron transfer was proposed as the key step for the reaction.

(PDF emailed within 0-6 h: $19.90)

Accession: 060018806

Download citation: RISBibTeXText

PMID: 28451308

DOI: 10.1039/c6sc04135c


Related references

An N-heterocyclic carbene-catalyzed [8 + 3] annulation of tropone and enals via homoenolate. Journal of Organic Chemistry 71(23): 8964-8965, 2006

Access to dihydropyridinones and spirooxindoles: application of N-heterocyclic carbene-catalyzed [3+3] annulation of enals and oxindole-derived enals with 2-aminoacrylates. Chemical Communications 53(44): 5985-5988, 2017

N-heterocyclic carbene-catalyzed reaction of chalcones and enals via homoenolate: an efficient synthesis of 1,3,4-trisubstituted cyclopentenes. Journal of the American Chemical Society 128(27): 8736-8737, 2006

N-heterocyclic carbene catalyzed homoenolate-addition reaction of enals and nitroalkenes: asymmetric synthesis of 5-carbon-synthon δ-nitroesters. Angewandte Chemie 51(33): 8276-8280, 2012

Asymmetric N-heterocyclic carbene catalyzed addition of enals to nitroalkenes: controlling stereochemistry via the homoenolate reactivity pathway to access δ-lactams. Journal of the American Chemical Society 135(23): 8504-8507, 2014

Enantioselective [3 + 2] Annulation of Enals with 2-Aminoacrylates Catalyzed by N-Heterocyclic Carbene. Organic Letters 19(14): 3943-3946, 2017

Bifunctional N-heterocyclic carbene catalyzed [3+4] annulation of enals and aurones. Chemistry 21(5): 1868-1872, 2014

N-Heterocyclic carbene-catalyzed diastereoselective synthesis of β-lactone-fused cyclopentanes using homoenolate annulation reaction. Chemical Communications 51(46): 9559-9562, 2016

An unexpected N-heterocyclic carbene-catalyzed annulation of enals and nitroso compounds. Journal of Organic Chemistry 74(4): 1744-1746, 2009

Asymmetric N-heterocyclic carbene (NHC)-catalyzed annulation of modified enals with enolizable aldehydes. Organic Letters 15(20): 5202-5205, 2013

A cascade reaction actuated by nucleophilic heterocyclic carbene catalyzed intramolecular addition of enals via homoenolate to α,β-unsaturated esters: efficient synthesis of coumarin derivatives. Organic Letters 15(1): 68-71, 2012

Asymmetric Synthesis of 4-Aryl-3,4-dihydrocoumarins by N-Heterocyclic Carbene Catalyzed Annulation of Phenols with Enals. Organic Letters 19(6): 1318-1321, 2017

Highly enantioselective γ-amination by N-heterocyclic carbene catalyzed [4+2] annulation of oxidized enals and azodicarboxylates. Angewandte Chemie 52(40): 10644-7, 2013

N-heterocyclic carbene catalyzed annulation of benzofuran-2,3-diones and enals: a concise synthesis of spiro-bis-lactone. Organic & Biomolecular Chemistry 11(34): 5634-5641, 2014

N-heterocyclic carbene catalyzed annulation of enals to aurone analogs: synthesis of cyclopentene-fused spirobenzofuran-3-ones. Organic Letters 16(24): 6374-6377, 2014