Atom-Economical and Metal-Free Synthesis of Multisubstituted Furans from Intramolecular Aziridine Ring Opening

Abstract

Multisubstituted furans were prepared from dialkyl 2-(aziridin-2-ylmethylene)malonate and/or 1,3-dione through aziridine ring opening by the internal carbonyl oxygen with the assistance of BF 3 ·OEt 2 , followed by aromatization. This synthetic method is free from any metal and is atom-economical with all of the atoms in the starting material retained in the final product.

A short and efficient formal synthesis of (R)-pipecolic acid from the ring expansion of chiral aziridine

“…1). Activated aziridines are quite reactive towards ring opening reaction without further activation [13,14], while non-activated aziridine is quite stable and inert to the nucleophiles, unless it is activated as an aziridinium ion (Scheme 1) [15][16][17][18][19][20][21]. Activation of aziridine nitrogen with external electrophile (3a) followed by ring opening reaction results in the formation of acyclic compound 4.…”

Atom Economical Multi-Substituted Pyrrole Synthesis from Aziridine

“…In this report, we describe an atom economical synthesis of multi-substituted pyrroles from regiospecific aziridine ring-opening by various nucleophiles [ 23 , 24 , 25 , 26 ] and the following cyclization in Knorr-type reactions.…”

Discovery of (E)-2-Methoxyethene-1-sulfonyl Fluoride for the Construction of Enaminyl Sulfonyl Fluoride

“…In the current scenario of chemical synthesis around the world, the term “green chemistry” is well acknowledged in both academia and the chemical industry . The concept of green chemistry is to design chemical products and processes that are more environmentally benign and reduce the negative impacts on human health and the environment. , Green synthesis protocols not only provide essential atom economy, , energy savings, waste reduction, and easy workup, but also avoid hazardous chemicals . Therefore, there is an urgent need to synthesize biologically meaningful molecules through green protocols.…”