+ Site Statistics
+ 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

Nucleophilic heterocyclic carbene catalyzed annulation of enals to chalcones in methanol: a stereoselective synthesis of highly functionalized cyclopentanes

Nucleophilic heterocyclic carbene catalyzed annulation of enals to chalcones in methanol: a stereoselective synthesis of highly functionalized cyclopentanes

Organic Letters 11(12): 2507-2510

Homoenolates generated from enals by nucleophilic heterocyclic carbene (NHC) catalysis undergo annulation with chalcones in methanol to afford methyl beta-hydroxycyclopentanecarboxylates, stereoselectively. Construction of four contiguous stereocenters in a stereoselective manner is noteworthy.

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

Accession: 054683717

Download citation: RISBibTeXText

PMID: 19459619

DOI: 10.1021/ol900571x

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

Stereoselective Synthesis of Functionalized Tetrahydro-1H-1,2-diazepines by N-Heterocyclic Carbene-Catalyzed [3 + 4] Annulation. Organic Letters 19(19): 5380-5383, 2017

N-Heterocyclic carbene-catalyzed annulation of cyclic β-enamino esters with enals: access to functionalized indolo[2,3-a]quinolizidines. Organic & Biomolecular Chemistry 13(16): 4661-4667, 2015

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

A highly regio- and stereoselective cascade annulation of enals and benzodi(enone)s catalyzed by N-heterocyclic carbenes. Angewandte Chemie 50(8): 1910-1913, 2011

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

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

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

Highly stereoselective synthesis of functionalized pyrrolo[3,2-c]quinolines via N-heterocyclic carbene catalyzed cascade sequence. Organic Letters 16(19): 5048-5051, 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

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 (NHC) three-component domino reactions: highly stereoselective synthesis of functionalized acyclic ε-ketoesters. Organic & Biomolecular Chemistry 9(6): 1791-1798, 2011

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

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, 2016