benign method is advantageous from a green chemical viewpoint with regard to yield, substrates variation, reagent availability, and simple procedures. This method was applied to a short step formal synthesis of (R)-muscone, a natural macrocyclic musk.
Acylation of Unsaturated Halides, Alcohols, Esters and Ketones
作者:Didier Barbry、Catherine Faven、Aziz Ajana
DOI:10.1080/00397919308013794
日期:1993.11
Abstract treatment of the title compounds with acyl halide and Lewis acid affords unsaturatedketones (mainly α-β with aluminium chloride, selectively β-γ with silver tetrafluoroborate). Reduction of the alkenyl group gives polyfunctional ketones.
The present invention relates to a compound represented by the following formula (1):
wherein W, X, Y, R
1
, R
2
, R
33
, R
34
, m and n are as defined in the claims, or a pharmacologically acceptable salt thereof.
Synthesis of ω-Hydroxy Carboxylic Acids and α,ω-Dimethyl Ketones Using α,ω-Diols As Alkylating Agents
作者:Yosuke Iuchi、Megumi Hyotanishi、Brittany E. Miller、Kensaku Maeda、Yasushi Obora、Yasutaka Ishii
DOI:10.1021/jo9027165
日期:2010.3.5
Synthesis of omega-hydroxy carboxylic acids and alpha,omega-dimethyl diketones was successfully achieved by using alpha,omega-diols as alkylating agents under the influence of an iridium catalyst. For example, the alkylation of butyl cyanoacetate with 1,13-tridecanediol in the presence of [IrCl(cod)](2) or [IrCl(coe)(2)](2) gave rise to butyl 2-cyano-15-hydroxypentadecanoate in good yield which is easily converted to cyclopentadecanolide (CPDL). In addition, the alkylation of acetone with 1,10-decanediol in the presence of [IrCl(cod)](2) and KOH resulted in an important muscone precursor, 2,15-hexadecanedione (HDDO), in good yield.
Canonica; Bacchetti, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1953, vol. <8>15, p. 278,281