1193-55-1Relevant articles and documents
Acid Chlorides as Formal Carbon Dianion Linchpin Reagents in the Aluminum Chloride-Mediated Dieckmann Cyclization of Dicarboxylic Acids
Armaly, Ahlam M.,Bar, Sukanta,Schindler, Corinna S.
, p. 3962 - 3965 (2017)
The development of acid chlorides as formal dianion linchpin reagents that enable access to cyclic 2-alkyl- and 2-acyl-1,3-alkanediones from dicarboxylic acids is described herein. Mechanistic experiments relying on 13C-labeling studies confirm the role of acid chlorides as carbon dianion linchpin reagents and have led to a revised reaction mechanism for the aluminum(III)-mediated Dieckmann cyclization of dicarboxylic acids with acid chlorides.
Design, synthesis and application of spiro[4.5]cyclohexadienonesviaone-pot sequentialp-hydroxybenzylation/oxidative dearomatization
Patil, Vaibhav B.,Nanubolu, Jagadeesh Babu,Chegondi, Rambabu
supporting information, p. 5574 - 5577 (2021/06/12)
One-pot sequentialp-hydroxybenzylation/oxidative dearomatization/spiroannulation has been designed for the efficient construction of tetrahydrofuran containing spiro-cyclohexadienones. This reaction proceeds through thep-hydroxybenzylation of 1,3-diketones withp-hydroxybenzyl alcoholviaquinone methide formation followed by oxidative dearomatization/spiroannulation with suitable alcohols. The Friedel-Crafts alkylation of spiro[4.5]cyclohexadienones with indoles provided a broad array of highly diastereoselective C-3 alkylated spirocycles and cyclohepta[b]indoles depending upon the ring size of the fused cyclic ketones.
Aluminum Chloride-Mediated Dieckmann Cyclization for the Synthesis of Cyclic 2-Alkyl-1,3-alkanediones: One-Step Synthesis of the Chiloglottones
Armaly, Ahlam M.,Bar, Sukanta,Schindler, Corinna S.
supporting information, p. 3958 - 3961 (2017/08/15)
Cyclic 2-alkyl-1,3-alkanediones are ubiquitous structural motifs in many natural products of biological importance. Reported herein is an AlCl3·MeNO2-mediated Dieckmann cyclization reaction of general synthetic utility that enables direct access to complex 2-alkyl-1,3-dione building blocks from readily available dicarboxylic acid and acid chloride substrates. This new strategy enables direct synthetic access to the chiloglottone plant pheromones from commercial material in a single synthetic transformation.
