Nitroalkenes as Carbonyl Surrogates in Arylmethyl-homoallylic Alcohol Forming One-Pot Allylation Reactions in Water

Abstract

A simple and practical approach has been developed for conducting direct, homoallylic alcohol forming allylation reactions of nitroalkenes in water. Employing the new method, various arylmethyl-homoallylic alcohols can be produced from the corresponding, readily prepared β-nitrostyrenes.

Tin Powder-Promoted Cascade Condensation/Allylation/Lactamization: Synthesis of Isoindolinones and Pyrazoloisoindol-8-ones

“…These indicated that the side product 5a was formed through deacylation/cyclation of acylhydrazone 12a in the presence of in situ formed tin salts. Thus, a possible mechanism was proposed as in Scheme on the basis of our experiment results and the literature . Acylhydrazones 12 were formed from condensation of 2-formylbenzoic acids 1 and hydrazides 2 , and nucleophilic addition of in situ formed organotin reagents 14 to acylhydrazones 12 produced intermediates 16 , which were then cyclized to afford products 4 .…”

“…This method not only kept the advantages of organotin reagents, but also avoided the use of toxic allylstannanes. Afterward, tin powder-promoted organic reactions have been studied widely by organic chemists . These advantages encouraged us to investigate the application of tin powder-promoted reactions in the construction of nitrogen-containing heterocycles.…”

Tin powder‐promoted diastereoselective allylation of chiral acylhydrazones

“…Afterwards, more and more attention has been paid to tin powder‐promoted reactions. Especially, some reactions could be carried out in the presence of water or in pure water . This technique avoided the use of toxic stannanes while retaining their merits such as moisture stability, tolerance to functional groups and high selectivity .…”

Synthesis of homoallylic amines and acylhydrazides by tin powder‐promoted multicomponent one‐pot allylation reactions

“…Subsequently, allylations mediated by metallic tin were investigated in the presence of water or just using water as solvent, but most studies focused on allylation of aldehydes. [31,[51][52][53][54][55] Some other substrates such as nitroalkenes, [11] enol ethers [56] and aldoximes [57] were also allylated using allylic bromide and metallic tin in water to give homoallylic alcohols.…”