57740-07-5Relevant articles and documents
The study of intramolecular tandem radical cyclizations of acylsilanes with radicalphiles attached on silicon
Tang, Kuo-Hsiang,Liao, Fang-Yu,Tsai, Yeun-Min
, p. 2037 - 2045 (2005)
Radical cyclizations of acylsilanes with radicalphilic pendant introduced on silicon proceeded in a tandem fashion to give spiro products containing a cyclic silyl ether skeleton. Because the alkoxysilyl group can be replaced with a hydroxy group through
A general electron transfer reduction of lactones using SmI 2-H2O
Szostak, Michal,Collins, Karl D.,Fazakerley, Neal J.,Spain, Malcolm,Procter, David J.
supporting information; experimental part, p. 5820 - 5824 (2012/08/28)
Herein we describe a strategy for the selective, electron transfer reduction of lactones of all ring sizes and topologies using SmI 2-H2O and a Lewis base to tune the redox properties of the complex. The current protocol permits instantaneous reduction of lactones to the corresponding diols in excellent yields, under mild reaction conditions and with useful chemoselectivity. We demonstrate the broad utility of this transformation through the reduction of complex lactones and sensitive drug-like molecules. Sequential electron transfer reactions and syntheses of deuterated diols are also described.
Grignard reagents: Alkoxide-directed iodine-magnesium exchange at sp 3 centers
Fleming, Fraser F.,Gudipati, Subrahmanyam,Vu, Viet Anh,Mycka, Robert J.,Knochel, Paul
, p. 4507 - 4509 (2008/03/11)
(Chemical Equation Presented) Sequential addition of i-PrMgCl and BuLi to sp3 hybridized iodoalcohols triggers a facile iodine-metal exchange. Intercepting the resulting cyclic Grignard reagents with a slight excess of an electrophile leads to a diverse range of substituted alcohols. The iodine-magnesium exchange strategy is effective with 3-carbon iodoalcohols bearing alkyl substitutents on the carbinol or adjacent carbons and with the chain-extended homolog 4-iodobutan-1-ol.
3-chloropropyl and 4-chlorobutyl phenyl ethers as sources of 1,3-dilithiopropane and 1,4-dilithiobutane: Sequential reaction with carbonyl compounds
Foubelo, Francisco,Saleh, Sadiq A.,Yus, Miguel
, p. 3478 - 3483 (2007/10/03)
The reaction of 3-chloropropyl and 4-chlorobutyl phenyl ethers (1) with lithium powder and a catalytic amount of DTBB (5% molar) in THF at - 78 °C followed by successive treatment with a carbonyl compound [R1R2CO = ButCHO, Me2CO, (CH2)5CO, (-)-menthone] at -78 to 20 °C and, after 1.5 h at this temperature, with a second one [R3R4CO = Bu1CHO, PhCHO, Me2CO, MeCOPrn, (CH2)5CO, (-)-menthone] at -78 °C leads, after hydrolysis with water, to the corresponding 1,5-and 1,6-diols (2). Because of the competition of two different reductive cleavages, 1,4- and 1,5-diols 3 were also obtained as side-reaction products.
Group transfer from silicon to carbon via tandem radical cyclizations of acylsilanes
Tsai, Yeun-Min,Tang, Kuo-Hsiang,Jiaang, Weir-Torn
, p. 7767 - 7770 (2007/10/03)
Tandem radical cyclizations of acylsilanes with alkene or alkyne functionalities attached to silicon afforded cyclic silyl ethers which were oxidatively hydrolyzed to give diols or ketone alcohols.
One-Step Annelation. A Convenient Method for the Preparation of Diols, Spirolactones, and Spiroethers from Lactones
Canonne, Persephone,Foscolos, Georges B.,Belanger, Denis
, p. 1828 - 1835 (2007/10/02)
1-(ω-Hydroxyalkyl)cyclopentanols and -cyclohexanols were prepared in one step in high yields from butane-1,4-diyl- and pentane-1,5-diylmagnesium dibromides and lactones in tetrahydrofuran.This method was found to be general and applicable to lactones of any size (β, γ, δ, and ε) and structure whether aliphatic, aromatic, bicyclic, or spirocyclic.Evidently important steric hindrance close to the carbonyl group prevents annelation and attack on the second nucleophilic center of the Grignard reagent.Furthermore, in the case of oxetan-2-one one obtains, in additionto the corresponding diol, products resulting from scission of the C-O bond.The diols by appropriate transformation afford new routes to spirolactones and spiroethers.
