+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Chiral N-heterocyclic carbene catalyzed annulation of α,β-unsaturated aldehydes with 1,3-dicarbonyls



Chiral N-heterocyclic carbene catalyzed annulation of α,β-unsaturated aldehydes with 1,3-dicarbonyls



Chemical Communications 47(30): 8670-8672



Chiral N-heterocyclic carbene catalyzed annulations of ynals and enals with 1,3-dicarbonyls have been described. The two reactions provided direct and efficient methods for enantioselective synthesis of functionalized dihydropyranones. Comparatively, the reactions starting from ynals were atom-economical; furthermore the reactions of enals demonstrated broader substrate compatibility.

Please choose payment method:






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

Accession: 052063365

Download citation: RISBibTeXText

PMID: 21709880

DOI: 10.1039/c1cc12778k


Related references

N-Heterocyclic Carbene/Lewis Acid Catalyzed Enantioselective Aerobic Annulation of α,β-Unsaturated Aldehydes with 1,3-Dicarbonyl Compounds. Journal of Organic Chemistry 81(14): 6136-6141, 2016

Chiral N-heterocyclic carbene-catalyzed generation of ester enolate equivalents from {alpha},{beta}-unsaturated aldehydes for enantioselective Diels-Alder reactions. Proceedings of the National Academy of Sciences of the United States of America 107(48): 20661-5, 2010

Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes. Synthesis 47(3): 421-428, 2014

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

Oxidative N-heterocyclic carbene catalyzed stereoselective annulation of simple aldehydes and 5-alkenyl thiazolones. Chemical Communications 51(38): 8134-8137, 2015

Enantioselective N-Heterocyclic Carbene-Catalyzed [3+3] Annulation of ,-Unsaturated Esters with Methyl Ketoimine. Advanced Synthesis & Catalysis 358(11): 1864-1869, 2016

N-Heterocyclic Carbene Catalyzed Sulfenylation of α,β-Unsaturated Aldehydes. Organic Letters 18(21): 5708-5711, 2016

N-Heterocyclic Carbene-Catalyzed δ-Carbon LUMO Activation of Unsaturated Aldehydes. Journal of the American Chemical Society 137(17): 5658-5661, 2015

N-Heterocyclic Carbene-Catalyzed Annulation of α-Chloroaldehydes with γ-/δ-Amino-α,β-Unsaturated Ketones: Enantioselective Synthesis of Pyrrolidones and Piperidones. Chemistry 24(33): 8302-8305, 2018

N-heterocyclic carbene (NHC)-catalyzed/Lewis acid mediated conjugate umpolung of alkynyl aldehydes for the synthesis of butenolides: a formal [3+2] annulation. Chemistry 19(13): 4146-4150, 2013

Chiral spirooxindole-butenolide synthesis through asymmetric N-heterocyclic carbene-catalyzed formal (3 + 2) annulation of 3-bromoenals and isatins. Organic Letters 16(19): 5028-5031, 2014

N-heterocyclic carbene catalyzed reactions of α-bromo-α,β-unsaturated aldehydes/α,β-dibromoaldehydes with 1,3-dinucleophilic reagents. Chemistry 18(7): 1914-1917, 2012

Enantioselective N-heterocyclic carbene-catalyzed Michael addition to α,β-unsaturated aldehydes by redox oxidation. Organic Letters 13(15): 4080-4083, 2011

N-Heterocyclic Carbene-Catalyzed Olefination of Aldehydes with Vinyliodonium Salts To Generate α,β-Unsaturated Ketones. Organic Letters 20(7): 1906-1909, 2018

N-Heterocyclic Carbene-Catalyzed Oxidative Annulations of α,β-Unsaturated Aldehydes with Hydrazones: Selective Synthesis of Optically Active 4,5-Dihydropyridazin-3-ones and Pyridazin-3-ones. Journal of Organic Chemistry 80(12): 6350-6359, 2015