+ 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

Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes



Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes



Synthesis 47(3): 421-428



Diastereo- and enantioselective N-heterocyclic carbene catalyzed 1-azadiene Diels-Alder reactions of (E)-2-styrylbenzothiazoles with α-chloro aldehydes are reported. This annulation strategy provides an efficient access to medicinally important dihydrobenzothiazolopyridin-1-ones in good to excellent yields (44-97%) with very good to excellent stereoselectivities (up to 9:1 dr, 98% ee) and tolerates quite a range of substituents.

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

Accession: 057260784

Download citation: RISBibTeXText

PMID: 26752795

DOI: 10.1055/s-0034-1379369


Related references

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

Chiral N-heterocyclic carbene catalyzed annulation of α,β-unsaturated aldehydes with 1,3-dicarbonyls. Chemical Communications 47(30): 8670-8672, 2011

Oxidative Asymmetric [2 + 3] Annulation of Aldehydes with Azomethine Imines Enabled by N-Heterocyclic Carbene Catalysis. Organic Letters 19(22): 6100-6103, 2017

N-heterocyclic carbene catalyzed enantioselective α-fluorination of aliphatic aldehydes and α-chloro aldehydes: synthesis of α-fluoro esters, amides, and thioesters. Angewandte Chemie 54(2): 660-663, 2016

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

Asymmetric synthesis of pyrroloindolones by N-heterocyclic carbene catalyzed [2+3] annulation of α-chloroaldehydes with nitrovinylindoles. Angewandte Chemie 52(51): 13562-6, 2013

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

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 (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 [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

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

N-heterocyclic-carbene-catalyzed asymmetric oxidative hetero-Diels-Alder reactions with simple aliphatic aldehydes. Angewandte Chemie 51(49): 12330-3, 2013

N-Heterocyclic Carbene Catalyzed [4 + 2] Annulation Reactions with in Situ Generated Heterocyclic ortho-Quinodimethanes. Organic Letters 18(15): 3822-3825, 2016

N-heterocyclic carbene-promoted annulation reaction of allenals with chalcones: synthesis of polysubstituted pyranyl aldehydes. Organic Letters 16(18): 4742-4745, 2014