Herein, we report a highly facile and unprecedented activation of 3-amido oxetanes to synthesize 2-oxazoline amide ethers using a transient electrophilic aza-oxyallyl cation as an activating as well as an alkylating agent under mild reaction conditions. The aza-oxyallyl cation driven intramolecular rearrangement of 3-amido oxetanes to 2-oxazolines is the hallmark of this transformation and is a new addition to the reactivity profile of aza-oxyallyl cations.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.1c03108DOI Listing

Publication Analysis

Top Keywords

aza-oxyallyl cation
12
cation driven
8
amide ethers
8
3-amido oxetanes
8
aza-oxyallyl
4
driven 3-amido
4
3-amido oxetane
4
oxetane rearrangement
4
rearrangement 2-oxazolines
4
2-oxazolines access
4

Similar Publications

Here, we report an efficient transition-metal-free C(sp)-C(sp) Suzuki-Miyaura-type cross-coupling between α-halo Weinreb-type amides and arylboronic acids. The reaction is carried out by capturing active aza-oxyallyl cation (AOAC) with arylboronic acid to form a boron "ate" complex, followed by 1,4-migration to give α-aryl amides with good yields.

View Article and Find Full Text PDF

Herein, we report the first general approach to access -alkoxy-2,2-difluoro indoxyls, via formal 3 + 2 cycloaddition of aryne and (putative) fluorinated-aza-oxyallyl cation. This transition-metal/oxidant-free transformation occurs under mild reaction conditions with a short reaction time. Mechanistic investigation indicates the possible involvement of the closed form of fluorinated-aza-oxyallyl cation, viz.

View Article and Find Full Text PDF

Access to 1,3-functionalized azetidines through a diversity-oriented approach is highly sought-after for finding new applications in drug-discovery. To this goal, strain-release-driven functionalization of azabicyclo[1.1.

View Article and Find Full Text PDF

Herein, we report a highly efficient and unprecedented approach for heteroarylation of congested α-bromoamides via electrophilic aromatic substitution of imidazo-heteroarenes and indolizines under mild reaction conditions (room temperature, metal, and oxidant free). The participation of an in situ generated aza-oxyallyl cation as an alkylating agent is the hallmark of this transformation. The method was readily adapted to synthesize novel imidazo-heteroarene-fused dibenzoazepinone architectures of potential medicinal value.

View Article and Find Full Text PDF

Herein, we report a highly facile and unprecedented activation of 3-amido oxetanes to synthesize 2-oxazoline amide ethers using a transient electrophilic aza-oxyallyl cation as an activating as well as an alkylating agent under mild reaction conditions. The aza-oxyallyl cation driven intramolecular rearrangement of 3-amido oxetanes to 2-oxazolines is the hallmark of this transformation and is a new addition to the reactivity profile of aza-oxyallyl cations.

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!