15972-17-5Relevant academic research and scientific papers
One-Pot γ-Lactonization of Homopropargyl Alcohols via Intramolecular Ketene Trapping
Yamane, Daichi,Tanaka, Haruna,Hirata, Akihiro,Tamura, Yumiko,Takahashi, Daichi,Takahashi, Yusuke,Nagamitsu, Tohru,Ohtawa, Masaki
supporting information, p. 2831 - 2835 (2021/05/05)
A one-pot γ-lactonization of homopropargyl alcohols via an alkyne deprotonation/boronation/oxidation sequence has been developed. Oxidation of the generated alkynyl boronate affords the corresponding ketene intermediate, which is trapped by the adjacent hydroxy group to furnish the γ-lactone. We have optimized the conditions as well as examined the substrate scope and synthetic applications of this efficient one-pot lactonization.
Photocatalytic Synthesis of γ-Lactones from Alkenes: High-Resolution Mass Spectrometry as a Tool to Study Photoredox Reactions
Triandafillidi, Ierasia,Kokotou, Maroula G.,Kokotos, Christoforos G.
supporting information, p. 36 - 39 (2018/01/17)
A mild photocatalytic manifold for the synthesis of γ-lactones has been developed. Utilizing Ru(bpy)3Cl2 as the photocatalyst, a cheap and reproducible synthetic protocol for γ-lactones has been introduced. Mechanistic studies revealed the successful monitoring of photocatalytic reactions and radical intermediates via high-resolution mass spectrometry.
(HMe 2 SiCH 2) 2: A Useful Reagent for B(C 6 F 5) 3 -Catalyzed Reduction-Lactonization of Keto Acids: Concise Syntheses of (-)- cis -Whisky and (-)- cis -Cognac Lactones
Xie, Hengmu,Lu, Ji,Gui, Yingying,Gao, Lu,Song, Zhenlei
supporting information, p. 2453 - 2459 (2017/10/06)
(HMe 2 SiCH 2) 2 has been utilized as a useful reagent for B(C 6 F 5) 3 -catalyzed reduction-lactonization of keto acids to synthesize γ- and δ-lactones. The process led concisely to (-)- cis -whisky and (-)- cis -cognac lactones in respective overall yields of 32% and 36%.
Efficient synthesis of γ-lactones via gold-catalyzed tandem cycloisomerization/oxidation
Shu, Chao,Liu, Meng-Qi,Sun, Yu-Zhe,Ye, Long-Wu
supporting information, p. 4958 - 4961,4 (2012/12/12)
A novel Au-catalyzed tandem cycloisomerization/oxidation of homopropargyl alcohols was developed. Various γ-lactones can be accessed readily by utilizing this strategy. Notably, the mechanism of this reaction is distinctively different from the related Ru-catalyzed reactions where the ruthenium vinylidene intermediate was proposed.
Efficient synthesis of γ-lactones via gold-catalyzed tandem cycloisomerization/oxidation
Shu, Chao,Liu, Meng-Qi,Sun, Yu-Zhe,Ye, Long-Wu
supporting information, p. 4958 - 4961 (2013/01/15)
A novel Au-catalyzed tandem cycloisomerization/oxidation of homopropargyl alcohols was developed. Various γ-lactones can be accessed readily by utilizing this strategy. Notably, the mechanism of this reaction is distinctively different from the related Ru-catalyzed reactions where the ruthenium vinylidene intermediate was proposed.
An asymmetric, SmI2-mediated approach to γ-butyrolactones using a new, fluorous-tagged auxiliary
Vogel, Johannes C.,Butler, Rebecca,Procter, David J.
experimental part, p. 11876 - 11883 (2009/04/06)
A new, fluorous-tagged chiral auxiliary has been developed for the asymmetric, SmI2-mediated coupling of aldehydes and α,β-unsaturated esters. γ-Butyrolactones are obtained in moderate to good isolated yield and in high enantiomeric excess. The fluorous tag allows the auxiliary to be conveniently recovered by fluorous solid-phase extraction (FSPE) and reused.
Preparation of titanated alkoxyallenes from 3-alkoxy-2-propyn-1-yl carbonates and (η2-propene)Ti(O-i-Pr)2 as an efficient ester homoaldol equivalent
Hanazawa, Takeshi,Okamoto, Sentaro,Sato, Fumie
, p. 2369 - 2371 (2007/10/03)
(equation presented) 3-Alkoxy-2-propyn-1-yl carbonates (2) react with a divalent titanium reagent (η2-propene)Ti(O-i-Pr)2 to afford titanated alkoxyallenes 1 which, in turn, react with aldehydes regiospecifically to provide the corresponding γ-addition products in good to excellent yields, thus affording a convenient method for synthesizing γ-hydroxy esters 3 and/or γ-butyrolactones 4.
An expeditious enantioselective synthesis of γ-lactones
Chong,Mar
, p. 1981 - 1984 (2007/10/02)
α-Alkoxyorganolithium reagents react with α,β-unsaturated trimethylhydrazides to give γ-alkoxytrimethylhydrazides in moderate to good yields. Acid hydrolysis of the latter compounds yields γ-lactones. A short enantioselective route to (S)-hexanolide is described.
A Direct Synthesis of γ-, δ-, and ε-Lactones Utilizing SmI2-induced Barbier-type Reaction in the Presence of Hexamethylphosphoric Triamide (HMPA)
Otsubo, Kenji,Kawamura, Kisa,Inanaga, Junji,Yamaguchi, Masaru
, p. 1487 - 1490 (2007/10/02)
By using an efficient reduction system of SmI2-THF-HMPA, the coupling reaction of β-, γ-, or δ-bromoesters with carbonyl compounds was completed within a minute at room temperature affording γ-, δ-, or ε-lactones, respectively, in good yields.Cp2ZrCl2 was also found to be effective for the coupling with ketones.
