AI Article Synopsis

  • The study shows that Lewis acids can effectively promote the reaction of 1,3-bis(silyl)propenes with aldehydes.
  • This method produces (E)-1,3-dienes with high stereoselectivity and yields that are generally good to excellent.
  • The process is noted for being mild, does not require a base, and is easy to perform.

Article Abstract

The Lewis acid-promoted addition of 1,3-bis(silyl)propenes to aldehydes to provide the corresponding (E)-1,3-dienes in excellent stereoselectivity and good to excellent yields is reported. The procedure is mild, base-free, and operationally straightforward.

Download full-text PDF

Source
http://dx.doi.org/10.1021/jo2013466DOI Listing

Publication Analysis

Top Keywords

lewis acid-promoted
8
acid-promoted addition
8
addition 13-bissilylpropenes
8
13-bissilylpropenes aldehydes
8
aldehydes route
4
route 13-dienes
4
13-dienes lewis
4
aldehydes provide
4
provide corresponding
4
corresponding e-13-dienes
4

Similar Publications

Regiodivergent formal [4+2] cycloaddition of nitrosoarenes with furanyl cyclopropane derivatives as 4π components.

Chem Commun (Camb)

December 2024

Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Julián Clavería 8, 33006-Oviedo, Spain.

Cyclopropanes are commonly used as valuable 3-carbon building blocks. Herein, we disclose a different reactivity pattern of furanyl cyclopropanes, which serve as a 4-carbon component in Lewis acid-promoted [4+2] cycloadditions with nitrosoarenes to afford 1,2-oxazine derivatives. Importantly, the regioselectivity of the cycloaddition reaction can be controlled by the appropriate choice of the Lewis acid.

View Article and Find Full Text PDF

The synthesis of 1-azido -nucleosides is described to expand the set of azide-functionalized nucleosides for bioorthogonal applications and as potential antiviral drugs. Lewis acid-promoted azidation of a nucleoside hemiketal resulted in the formation of a tetrazole through a Schmidt reaction manifold. Conformational control to prevent ring-chain tautomerism enabled efficient 1-azidation with complete β-diastereoselectivity.

View Article and Find Full Text PDF

A simple and effective strategy for the construction of disulfide-substituted oxazole derivatives from amides, ynals, and acetyl disulfides via a Lewis acid-promoted three-component reaction has been reported. In addition, this reaction possesses other unique advantages, such as transition-metal-free catalysis, the production of disulfides, good functional group tolerance, and good regioselectivity.

View Article and Find Full Text PDF

Chemodivergent Reactions of Aromatic Ring-Annulated Hexahydrocyclopentafurans with Various Aldehydes.

Org Lett

November 2024

Applied Chemistry and Chemical Engineering, Graduate School of Engineering, Kogakuin University, Nakano 2665-1, Hachioji, Tokyo 192-0015, Japan.

Hexahydro-2-cyclopenta[]furan fused to electron-rich aromatic rings reacts with various aromatic aldehydes in different modes to build diverse frameworks. The reaction of a dimethoxybenzene-fused cyclopentafuran generated diquinanes fused with a hydrofuran ring, indenopyrans, or diarylindanes depending upon the type of aromatic aldehydes, whereas an indole-annulated cyclopentafuran generated another type of diquinane fused with hydrofuran ring or benzylidenecyclopentafuran. The chemodivergence is due to the different properties between indole- and dimethoxybenzene-fused hydrocyclopentafurans.

View Article and Find Full Text PDF

Lewis-Acid-Promoted Visible-Light-Mediated C(sp)-H Bond Functionalization of Arylvinylpyridines via Diradical Hydrogen Atom Transfer.

Org Lett

September 2024

Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, People's Republic of China.

A visible-light-induced intramolecular diradical-mediated hydrogen atom transfer (DHAT) of primary, secondary, and tertiary C(sp)-H bonds and subsequent cyclization is described. This transformation is enabled by triplet energy transfer upon Lewis acid coordination to alkyl-substituted arylvinylpyridines and gives access to a variety of benzocyclobutenes (>40 examples, 32-96% yield). Notably, tri- and tetrasubstituted olefins with tertiary C(sp)-H bonds effectively delivered sterically hindered products with adjacent all-carbon quaternary centers.

View Article and Find Full Text PDF

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!