103648-08-4Relevant articles and documents
HIGH YIELD ACYL ANION TRANSFER REACTIONS: NUCLEOPHILIC ACYLATION OF ALDEHYDES
Seyferth, Dietmar,Weinstein, Robert M.,Wang, Wei-Liang,Hui, Richard C.
, p. 4907 - 4910 (1983)
Aldehydes be may acylated to give R'CH(OH)C(O)R in good yield by the RLi/CO in situ procedure at very low temperatures.Examples are given of ketone acylations which demonstrate the advantages of 1:1 RLi/substrate stoichiometry and the use of lower (-135 deg C) temperature.
Imidoyllithiums: Masked acyllithium reagents
Alonso, Emma,Ramon, Diego J.,Miguel, Yus
, p. 8903 - 8906 (2007/10/03)
The reaction of chloroimines 1 with an excess of lithium powder and a catalytic amount of naphthalene (4 mol %) in THF at -78°C leads to the corresponding imidoyllithium intermediates 2, which by treatment with different electrophiles [PriCHO, Bu(t)CHO, n-C5H11CHO, PhCHO, Et2CO, (CH2)5CO, EtOCOCl, MeOCSCl, n-C7H15CON(Me)OMe] at -78 to 20°C and final hydrolysis with water affords functionalysed imines 3. For starting material la is necessary to filter off the excess of lithium at the end of the lithiation step in order to get compounds 3, without filtration amines 4 are the reaction products isolated. Hydrolysis of compounds 3 either during chromatographic purification or by acidic hydrolysis (2 N HCl, THF) gives the expected functionalised ketones 5.