+ 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

Stereoselective Synthesis of Functionalized Tetrahydro-1H-1,2-diazepines by N-Heterocyclic Carbene-Catalyzed [3 + 4] Annulation



Stereoselective Synthesis of Functionalized Tetrahydro-1H-1,2-diazepines by N-Heterocyclic Carbene-Catalyzed [3 + 4] Annulation



Organic Letters 19(19): 5380-5383



An efficient N-heterocyclic carbene (NHC)-catalyzed asymmetric [3 + 4] annulation reaction of N-Ts hydrazones with 2-bromoenals has been developed. A series of functionalized tetrahydro-1H-1,2-diazepines with two consecutive stereocenters was obtained using NHCs as the catalyst in good yields with excellent diastereo- and enantioselectivities.

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

Accession: 060278691

Download citation: RISBibTeXText

PMID: 28949541

DOI: 10.1021/acs.orglett.7b02657


Related references

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 Formal [3 + 2] Annulation of α-Bromoenals with 3-Aminooxindoles: A Stereoselective Synthesis of Spirooxindole γ-Butyrolactams. Journal of Organic Chemistry 80(22): 11593-7, 2015

N-heterocyclic carbene-catalyzed stereoselective cascade reaction: synthesis of functionalized tetrahydroquinolines. Organic Letters 15(18): 4750-4753, 2014

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

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 cyclic β-enamino esters with enals: access to functionalized indolo[2,3-a]quinolizidines. Organic and Biomolecular Chemistry 13(16): 4661-4667, 2015

N-heterocyclic carbene-catalyzed cascade annulation reaction of o-vinylarylaldehydes with nitrosoarenes: one-step assembly of functionalized 2,3-benzoxazin-4-ones. Organic and Biomolecular Chemistry 10(20): 4088-4094, 2012

N-Heterocyclic Carbene Mediated Homoenolate Annulation of Benzofuran-2,3-diones: Stereoselective Synthesis of Bis-Spirofuranones. Synlett 25(06): 853-857, 2014

N-heterocyclic carbene catalyzed switchable reactions of enals with azoalkenes: formal [4 + 3] and [4 + 1] annulations for the synthesis of 1,2-diazepines and pyrazoles. Journal of the American Chemical Society 136(50): 17402-5, 2014

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

Facile Synthesis of 2,2-Diacyl Spirocyclohexanones via an N-Heterocyclic Carbene-Catalyzed Formal [3C + 3C] Annulation. Organic Letters 2019, 2019

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

Direct and Enantioselective Synthesis of N-H-Free 1,5-Benzodiazepin-2-ones by an N-Heterocyclic Carbene Catalyzed [3+4] Annulation Reaction. Chemistry 24(9): 2103-2108, 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