Recent Progress on Polyconjugated Nitrodienynes/Nitroenynes:Synthesis and Applications

Abstract

Polyconjugated nitrodienynes/nitroenynes as nitroolefin derivatives are good kind of electrophiles and have been widely used in organic synthesis. There are multiple reaction sites due to the conjugated system. Therefore, competitive reactions of regioselectivity in the reaction process are existence, such as 1,4-addition reaction, 1,6-addition reaction, and even 1,8-addition reaction. The recent progress of the synthesis of nitrodienynes/nitroenynes and their applications in organic synthesis are summarized.

Catalyst-Free 1,6-Conjugate Addition/Aromatization/Sulfonylation of para-Quinone Methides: Facile Access to Diarylmethyl Sulfones

“…To address these limitations, developing efficient, green, and sustainable strategies to construct diarylmethyl sulfones remains important and is challenging. In continuation of our interest in constructing functionalized molecules, − herein, we report a catalyst-free, facile, and efficient route for the synthesis of diarylmethyl sulfones from the readily available starting materials, sulfonyl hydrazides , and p -quinone methides ( p -QMs), − which are widely used in modern organic synthesis because of the assembly of carbonyl and olefinic moieties (Figure b).…”

Organocatalytic Remote Stereocontrolled 1,8-Additions of Thiazolones to Propargylic Aza-p-quinone Methides

“…Organocatalytic remote stereocontrol is an attractive strategy for the construction of stereocenters at certain positions far from reactive functional groups but overcomes the formidable challenge of controlling both the regiochemistry and the stereochemistry in the reaction of prochiral nucleophiles with electron-deficient conjugate systems . In this respect, the organocatalytic asymmetric 1,6-conjugate addition reactions have been paid much attention .…”