+ 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 [3 + 4] Annulation of Enals and Alkenyl Thiazolones: Enantioselective Synthesis of Thiazole-Fused ε-Lactones



N-Heterocyclic Carbene-Catalyzed [3 + 4] Annulation of Enals and Alkenyl Thiazolones: Enantioselective Synthesis of Thiazole-Fused ε-Lactones



Journal of Organic Chemistry 81(11): 4841-4846



The bifunctional N-heterocyclic carbene catalyzed [3 + 4] annulation of enals and 5-alkenyl thiazolones was developed, giving the corresponding thiazole-fused ε-lactones in high yields with excellent diastereoselectivties and enantioselectivities. The thiazole-fused ε-lactone could be isomerized to the spirocyclic thiazolone-cyclopentanone without erosion of enantioselectivity.

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

Accession: 058370742

Download citation: RISBibTeXText

PMID: 27159734

DOI: 10.1021/acs.joc.6b00313


Related references

N-heterocyclic carbene catalyzed [4+3] annulation of enals and o-quinone methides: highly enantioselective synthesis of benzo-ε-lactones. Angewandte Chemie 52(33): 8607-8610, 2013

Oxidative N-heterocyclic carbene catalyzed stereoselective annulation of simple aldehydes and 5-alkenyl thiazolones. Chemical Communications 51(38): 8134-8137, 2016

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

Enantioselective synthesis of spiro γ-butyrolactones by N-heterocyclic carbene (NHC)-catalyzed formal [3 + 2] annulation of enals with 3-hydroxy oxindoles. Organic and Biomolecular Chemistry 15(9): 2013-2019, 2017

Enantioselective [3 + 2] Annulation of Enals with 2-Aminoacrylates Catalyzed by N-Heterocyclic Carbene. Organic Letters 19(14): 3943-3946, 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 formal [3+2] annulation reaction of enals: an efficient enantioselective access to spiro-heterocycles. Angewandte Chemie 53(38): 10232-6, 2014

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

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

N-Heterocyclic carbene-catalyzed [4+2] annulation of β-methyl enals and cyclic trifluoromethyl ketimines for the asymmetric synthesis of dihydroquinazolinone derivatives. Chemical Communications 53(82): 11342-11344, 2017

Nucleophilic heterocyclic carbene catalyzed annulation of enals to chalcones in methanol: a stereoselective synthesis of highly functionalized cyclopentanes. Organic Letters 11(12): 2507-2510, 2009

N-Heterocyclic Carbene Catalyzed [4+2] Annulation of Enals via a Double Vinylogous Michael Addition: Asymmetric Synthesis of 3,5-Diaryl Cyclohexenones. Angewandte Chemie 56(22): 6241-6245, 2017

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

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