144979-12-4Relevant academic research and scientific papers
Lactone radical cyclizations and cyclization cascades mediated by SmI 2-H2O
Parmar, Dixit,Matsubara, Hiroshi,Price, Kieran,Spain, Malcolm,Procter, David J.
supporting information; experimental part, p. 12751 - 12757 (2012/09/05)
Unsaturated lactones undergo reductive radical cyclizations upon treatment with SmI2-H2O to give decorated cycloheptanes in a single highly selective operation during which up to three contiguous stereocenters are generated. Furthermore, cascade processes involving lactones bearing two alkenes, an alkene and an alkyne, or an allene and an alkene allow "one-pot" access to biologically significant molecular scaffolds with the construction of up to four contiguous stereocenters. The cyclizations proceed by the trapping of radical anions formed by electron transfer reduction of the lactone carbonyl.
Gold-catalysed cyclic ether formation from diols
Jiang, Xiaolu,London, Emma K.,Morris, David J.,Clarkson, Guy J.,Wills, Martin
supporting information; experimental part, p. 9828 - 9834 (2011/02/23)
Gold(I) and (III) salts have been found to be highly effective at the catalysis of ether formation from alcohols. Intramolecular ether formation of a 1,5-diol was also achieved, with a stereoselectivity that indicates that an SN1 mechanism predominates. In an attempt to form a seven-membered ring, a stable 14-membered dimer product was also formed. Attempts to control the diastereoselectivity of the reaction using a chiral anionic counterion did not give products with a high de.
Enantioselective synthesis of Indolizidines bearing quaternary substituted stereocenters via rhodium-catalyzed [2 + 2 + 2] cycloaddition of alkenyl Isocyanates and terminal alkynes
Lee, Ernest E.,Rovis, Tomislav
supporting information; body text, p. 1231 - 1234 (2009/04/07)
An enantioselective synthesis of Indolizidines bearing quaternary substituted stereocenters by way of a rhodium-catalyzed [2 + 2 + 2] cycloaddition of substituted alkenyl Isocyanates and terminal alkynes Is described. The reaction provides lactam products using aliphatic alkynes, whereas aryl alkynes give rise to vlnylogous amide products. Through modification of the phosphoramldlte llgand, high levels of enantloselectlvlty, regloselectlvlty, and product selectivity are obtained for both products.
A new entry to 1,5-keto esters and their 4,4-dideuterio derivatives via methylene chloride as methylene dianion equivalents
Lin, Kuo-Wei,Chen, G-Yih,Chen, Wei-Fan,Yan, Tu-Hsin
, p. 4759 - 4761 (2008/09/20)
(Chemical Equation Presented) This TiCl4-Mg promoted multicomponent coupling of various amides with CH2Cl2 and methyl acrylate represents an extremely simple and practical synthesis of 1,5-keto esters. The efficiency of this chemistry is illustrated by the very simple preparation of unusual 4,4-dideuterio- 1,5-keto esters.
Oxidative cleavage of the C-C bond of 3,6-dialkylcyclohexane-1,2-diones by cell suspension cultures of Marchantia polymorpha
Matsuura, Yoshitomo,Chai, Wen,Endoh, Etsuko,Suhara, Jyumpei,Hamada, Hiroki,Horiuchi, C. Akira
, p. 669 - 673 (2007/10/03)
Biotransformation of 3,6-dialkylcyclohexane-1,2-diones by cell suspension cultures of Marchantia polymorpha involves regio-selective oxidative cleavage of the C-C bond to give the corresponding oxocarboxylic acids shortened by one carbon unit. In the case of cyclohexane-1,2-dione, adipic acid was obtained.
A general and straightforward approach to α,ω-ketoesters
Babudri, Francesco,Fiandanese, Vito,Marchese, Giuseppe,Punzi, Angela
, p. 13513 - 13520 (2007/10/03)
Chemoselective cross-coupling reactions of monoesters of dicarboxylic acid chlorides with organocopper reagents derived from Grignard reagents, cuprous bromide, and lithium bromide, provide a simple and straightforward method for synthesizing a variety of ketoesters.
