[reaction: see text] In an effort to develop new ways of synthesizing polycyclic alkaloids, we successfully added silyl enol ethers, allylsilanes, and enamines to iminium ions generated from amides. Because of their higher oxidation state, such iminiums show a yet unexploited advantage of potential double cyclizations over standard Mannich monocyclizations. We report herein the first example of tethered nonaromatic carbon nucleophiles adding to activated amides for the generation of enaminals of various ring sizes, with endo- or exo-cyclic nitrogen.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol0516519 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Enantioselective Reductive Divinylation of Unactivated Alkenes by Nickel-Catalyzed Cyclization Coupling Reaction.
J Am Chem Soc
August 2021
State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou 730000, China.
Catalytic asymmetric dicarbofunctionalization of tethered alkenes has emerged as a promising tool for producing chiral cyclic molecules; however, it typically relies on aryl-tethered alkenes to form benzene-fused compounds. Herein, we report an enantioselective cross-electrophile divinylation reaction of nonaromatic substrates, 2-bromo-1,6-dienes. The approach thus offers a route to new chiral cyclic architectures, which are key structural motifs found in various biologically active compounds.
View Article and Find Full Text PDFThe extent of conformational rigidity determines hydration in nonaromatic hexacyclic systems.
J Phys Chem B
March 2011
Scientific Computing Research Unit and Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa.
We conducted an ultrasonic study of the hydration number for hexacyclic systems. We find from these experiments that cyclohexane-based molecules such as cyclohexanol and myo-inositol show a very small increase in hydration number despite the large difference in the number of hydroxyl groups present in each of the molecules. There is however a dramatic increase in hydration number when shifting from molecules with a cyclohexane frame to molecules with a cyclopyranose frame particularly glucose.
View Article and Find Full Text PDFAddition of tethered nonaromatic carbon nucleophiles to chemoselectively activated amides.
Org Lett
September 2005
Laboratoire de synthèse organique et de développement de stratégies de synthèse, Département de Chimie, Université de Sherbrooke, 2500 boulevard Université, Sherbrooke, Québec J1K 2R1, Canada.
[reaction: see text] In an effort to develop new ways of synthesizing polycyclic alkaloids, we successfully added silyl enol ethers, allylsilanes, and enamines to iminium ions generated from amides. Because of their higher oxidation state, such iminiums show a yet unexploited advantage of potential double cyclizations over standard Mannich monocyclizations. We report herein the first example of tethered nonaromatic carbon nucleophiles adding to activated amides for the generation of enaminals of various ring sizes, with endo- or exo-cyclic nitrogen.
View Article and Find Full Text PDFResidue- and sequence-selective binding of nonaromatic dipeptides by bis(beta-cyclodextrin) with a functional tether.
Chembiochem
June 2004
Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P R China.
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!