145102-57-4Relevant academic research and scientific papers
1,4-Addition reactions of bis(iodozincio)methane with α,β-unsaturated ketones
Matsubara, Seijiro,Arioka, Daisuke,Utimoto, Kiitiro
, p. 1253 - 1254 (1999)
A reaction of bis(iodozincio)methane with acyclic enones proceeded in 1,4-addition manner to afford zinc enolate of β-zinciomethylketone. In the case of the 1,4-addition reactions of bis(iodozincio)methane with 2- cyclohexen-1-one, an assistance by copper
Iron(III) mediated transformations of cyclopropyltrimethylsilyl ethers. Part 1. Free radical tandem ring expansion-cyclisation reactions for the rapid construction of bicyclic ring systems
Booker-Milburn, Kevin I.,Thompson, David F.
, p. 2315 - 2322 (1995)
Treatment of a number of cyclopropyl trimethylsilyl ethers with anhydrous ferric chloride in dry dimethylformamide leads to diastereoisomerically pure bicyclic chloro ketones by a novel tandem ring expansion-cyclisation sequence.The reaction is thought to proceed by a mechanism involving the intermediacy of a cyclopropyl alkoxy radical.
Synthesis of medium-sized bicyclic compounds by intramolecular cyclization of cyclic β-keto radicals generated from cyclopropanols using manganese(III) tris(pyridine-2-carboxylate) and its application to total synthesis of 10-isothiocyanatoguaia-6-ene
Iwasawa, Nobuharu,Funahashi, Masahiro,Hayakawa, Satoshi,Ikeno, Taketo,Narasaka, Koichi
, p. 85 - 97 (1999)
Bicyclic cyclopropanols having an olefinic side chain are oxidized-with manganese(III) tris(pyridine-2-carboxylate) to generate cyclic β-keto radicals with ring-expansion. These cyclize intramolecularly, affording bicyclic radical intermediates. The cycli
Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation
Vulovic, Bojan,Trmcic, Milena,Matovic, Radomir,Saicic, Radomir N.
supporting information, p. 9618 - 9621 (2019/12/24)
Unsaturated oxyallyl cations with a suitably positioned alkene bond undergo 5-exo-cyclization with the formation of vinylcyclopentane derivatives. Alkyne analogues provide allenes. The reaction proceeds with a moderate to excellent level of stereoselectiv
Synthesis of cyclopropyl silyl ethers and their facile ring opening by photoinduced electron transfer as key step in radical/radical cationic cascade reactions
Waske, Prashant A.,Mattay, Jochen
, p. 10321 - 10330 (2007/10/03)
Various ring-fused cyclopropyl silyl ethers with an benzylic, olefinic or acetylenic side chain have been synthesized. Upon oxidative photoinduced electron transfer (PET) the cyclopropane ring opens and forms a reactive β-keto radical, which undergoes intramolecular cyclization. In some cases we observed only formation of ring opened non-cyclized products. With olefinic side chain 5-exo-trig mode of cyclization rather than 6-endo-trig mode of cyclization takes place whereas in case of acetylenic side chain we observed 6-endo cyclization.
Regio- and stereoselective cyclization reactions of unsaturated silyl enol ethers by photoinduced electron transfer - Mechanistic aspects and synthetic approach
Hintz, Sandra,Mattay, Jochen,Van Eldik, Rudi,Fu, Wen-Fu
, p. 1583 - 1596 (2007/10/03)
Oxidative photoinduced electron transfer (PET) reactions have been performed with various silyl enol ethers and silyloxy-2H-chromones bearing an olefmic or silylacetylenic side chain. The reactions result in regioselective ring closure with the formation of bi- to tetracyclic ring systems with a well-defined ring juncture, e.g. perhydrophenanthrenones 13 or benzo-annellated xanthenones 24. Our investigations have focussed on the optimization of this cychzation method with regard to irradiation time and product yield. The irradiation times could be reduced by using the cosensitized PET method. Modifying the substrate at the silyl group led to enhanced yields. In addition, we found that solvent and pressure dependences are important tools, allowing control of the regiochemistry. Both the synthesis of 6-endo products by radical cationic reaction pathways, as well as 5-exo ring closure by radical intermediates was achieved. Mechanistic details, including findings from deuterium labelling experiments, are discussed.
INTRAMOLECULAR RADICAL CYCLIZATION OF SILYLACETYLENIC OR OLEFINIC α-IODO KETONES: APPLICATION TO THE TOTAL SYNTHESIS OF (+/-)-MODHEPHENE
Sha, Chin-Kang,Jean, Tsong-Shin,Wang, Deh-Chi
, p. 3745 - 3748 (2007/10/02)
Silylacetylenic or olefinic α-iodo ketones were treated with tributyltin hydride and AIBN to give bicyclic ketones by an intramolecular α-carbonyl radical cyclization reaction.As an application of this radical cyclization reaction, the total synthesis of
