3908-31-4Relevant academic research and scientific papers
A Construction of α-Alkenyl Lactones via Reduction Radical Cascade Reaction of Allyl Alcohols and Acetylenic Acids
Zhang, Hua,Zhang, Guo-Min,He, Shuai,Shi, Zhi-Chuan,Zhang, Xiao-Mei,Wang, Ji-Yu
supporting information, p. 8337 - 8344 (2020/11/03)
An iron-catalyzed cascade reaction of radical reduction of allyl alcohols and acetylenic acids to construct polysubstituted α-alkenyl lactones has been developed. In this paper, various allyl alcohols can form allyl ester intermediates and are further transformed into alkyl radicals, which form products through intramolecular reflex-Michael addition. In addition, this method can be used to prepare spirocycloalkenyl lactones. Interestingly, this protocol can be used to synthesize the skeleton structure of natural products. Moreover, the product can be further transformed into a β-methylene tetrahydrofuran and tetrahydrofuran diene.
Iron(III) Chloride/Phenylsilane-Mediated Cascade Reaction of Allyl Alcohols with Maleimides: Synthesis of Poly-Substituted γ-Butyrolactones
Zhang, Hua,Zhan, Xiao-Yu,Chen, Xu-Ling,Tang, Lei,He, Shuai,Shi, Zhi-Chuan,Wang, Yu,Wang, Ji-Yu
supporting information, p. 4919 - 4925 (2019/11/03)
A iron-catalyzed free radical cascade reaction of allyl alcohols with N-substituted maleimides for accessing poly-substituted γ-butyrolactones has been developed. In this protocol, various allyl alcohols can open N-substituted maleimide rings to form allyl ester intermediates, and the allyl ester intermediates can be converted into an allyl ester alkyl radicals and undergo intramolecular free radical addition cyclization to form a polysubstituted γ-butyrolactones. In this protocol, spiro γ-butyrolactone compounds can be also synthesized. Meanwhile, the strategy could be applied to further construct a fully substituted tetrahydrofuran. The reaction is not sensitive to oxygen or moisture and has been performed on gram-scale. (Figure presented.).
Efficient synthesis of 3-sulfolenes from allylic alcohols and 1,3-dienes enabled by sodium metabisulfite as a sulfur dioxide equivalent
Dang, Hang T.,Nguyen, Vu T.,Nguyen, Viet D.,Arman, Hadi D.,Larionov, Oleg V.
supporting information, p. 3605 - 3609 (2018/05/26)
We present herein an efficient and practical method for a gram scale synthesis of 3-sulfolenes using sodium metabisulfite as a safe, inexpensive, and easy to handle sulfur dioxide equivalent. Diversely-substituted 3-sulfolenes can be prepared by reacting a variety of 1,3-dienes or allylic alcohols with sodium metabisulfite in aqueous hexafluoroisopropanol (HFIP) or in aqueous methanol in the presence of potassium hydrogen sulfate. Advantageously, the method enables conversion of allylic alcohols directly to 3-sulfolenes, bypassing intermediate 1,3-dienes.
Synthesis of Macrocyclic Ketones through Catalyst-Free Electrophilic Halogen-Mediated Semipinacol Rearrangement: Application to the Total Synthesis of (±)-Muscone
Liu, Yi,Yeung, Ying-Yeung
supporting information, p. 1422 - 1425 (2017/03/23)
A series of macrocycles were successfully prepared using electrophilic halogen-mediated semipinacol rearrangement under mild conditions. Although the expansion from small ring to medium ring is an energetically unfavorable process, the electrophilic halog
Arene-catalysed reductive desulfonylation and desulfinylation reactions: New routes for alkyllithiums
Alonso, Emma,Guijarro, David,Yus, Miguel
, p. 2699 - 2708 (2007/10/02)
The reactions of alkyl phenyl sulfones (1) with an excess of lithium powder and a catalytic amount of naphthalene (8 mol %) in the presence of a carbonyl compound or chlorotrimethylsilane (Barbier-type conditions) in THF at temperatures ranging between -78 and 20°C leads, after hydrolysis, to the expected products (2) arising from the corresponding alkyllithium generated in situ. When the same methodology is applied to sulfolene (3) or different alkyl phenyl sulfoxides (6), cyclic sulfinates 5 or products 2 are, respectively, obtained, the yields being, in general modest.
AN EPISULFONIUM ION MEDIATED RING EXPANSION OF 1-ALKENYLCYCLOALKANOLS
Kim, Sunggak,Park, Jung Ho
, p. 6181 - 6184 (2007/10/02)
It has been found that TBDMS ethers of 1-alkenylcycloalkanols are readily rearranged to the ring expanded α-(1-phenylthioalkyl)cycloalkanones in high yields via episulfonoium ions.
Original Syntheses of Carbonyl Compounds and gem-Dihalocyclopropanes from β-Hydroxylalkylselenides
Krief,A.,Laboureur, J. L.,Dumont, W.
, p. 1549 - 1552 (2007/10/02)
β-hydroxyalkylselenides possessing two alkyl substituents on the carbon bearing the selenyl moiety react with dihalocarbenes generated from haloforms and thallous ethoxide or under phase transfer catalysis to produce ring enlarged ketones as the sole product in the first case, as the main product in the second.The reaction takes another course when the dihalocarbenes generated from haloforms and tBuOK or from trihalomethylphenylmercury are employed and leads inter alias to dihalocyclopropanes.
Photooxygenation of 1-Vinylcycloalkenes. The Competition between "Ene" Reaction and Cycloaddition of Singlet Oxygen
Herz, Werner,Juo, Rouh-Rong
, p. 618 - 627 (2007/10/02)
The competition between the "ene" reaction and 1,4-cycloaddition reaction of 1O2 in a series of 1-vinylcycloalkenes (n = 5-10, 12) and 1-isopropenylcycloalkenes (n = 6-8) was studied.Ring size had a profound effect.When n = 5 or 7, products of the "ene" reaction predominated, but as ring size increased cycloaddition competed closely with the "ene" process, the crossover being at ring size 10. 1-Vinylhexenes constituted an exception with 1,4-cycloaddition greatly predominant. "Ene" products were almost exclusively conjugated diene hydroperoxides or secondary products derived from them; small amounts of unconjugated diene hydroperoxides were formed only when n = 9, 10, or 12.The influence of ring size of the "ene" to cycloaddition product ratio is compared with the rates of photooxygenation and the degree of syn-regiospecificity exhibited by (Z)-1-methylcycloalkenes and attributed to the same mainly conformational factors, as is the geometry of the "ene" products.The 1,4-cycloaddition products were converted to furans by means of ferrous sulfate.
Transformation of Carbon-Oxygen into Carbon-Carbon Bonds Mediated by Low-Valent Nickel Species
Wenkert, Ernest,Michelotti, Enrique L.,Swindell, Charles S.,Tingoli, Marco
, p. 4894 - 4899 (2007/10/02)
The substitution of alkoxy groups of enol ethers (1-methoxycyclohexenes, 1-methoxy-1-alkenes, and benzofuran) and aryl ethers (methoxynaphthalenes, cresyl methyl ethers, and dimethoxybenzenes) by hydrogen, alkyl groups, and aryl units, through Grignard reactions catalyzed by bis(triphenylphosphine)nickel dichloride or nickel dichloride, is described.The stereochemistry of the new reaction is portrayed, especially in connection with processes involving ring opening of dihydropyrans and dihydrofurans.The reaction has been applied to the synthesis of a termite trail pheromone and the acetate of the Douglas fir beetle aggregation pheromone.
