33046-84-3Relevant academic research and scientific papers
One-Pot Preparation of (E)-α,β-Unsaturated Aldehydes by a Julia-Kocienski Reaction of 2,2-Dimethoxyethyl PT Sulfone Followed by Acid Hydrolysis
Ando, Kaori,Watanabe, Haruka,Zhu, Xiaoxian
, p. 6969 - 6973 (2021/05/06)
(E)-α,β-Unsaturated aldehydes were synthesized by the Julia-Kocienski reaction of 2,2-dimethoxyethyl 1-phenyl-1H-tetrazol-5-yl (PT) sulfone 3 with various aldehydes, followed by acid hydrolysis. The reaction could be carried out in one pot, and various (E)-α,β-unsaturated aldehydes were obtained in a short time and with high yields.
Dehydrative Re2O7-Catalyzed Approach to Dihydropyran Synthesis
Lawrence, Jean-Marc I. A.,Floreancig, Paul E.
supporting information, p. 9513 - 9517 (2020/12/21)
Monoallylic 1,3- and 1,5-diols undergo Re2O7-mediated ionization to form allylic cations that engage in cyclization reactions to form dihydropyran products. The reactions give the 2,6-trans-stereoisomer as the major products as a result of minimizing steric interactions in a boat-like transition state. The results of these studies are consistent with cationic intermediates, with an intriguing observation of stereochemical retention in one example.
Cascade reaction including a formal [5?+?2] cycloaddition by use of alkyne-Co2(CO)6 complex
Sakata, Yuki,Yasui, Eiko,Mizukami, Megumi,Nagumo, Shinji
supporting information, p. 755 - 759 (2019/02/20)
A new cascade reaction including formal [5 + 2] cycloaddition was developed. Treatment of homocinnamyl alcohol and Co2(CO)6-complexed arylpropynal with BF3·OEt2 resulted in the generation of hydrobenzocyclohepta
Stereodivergence in the Ireland-Claisen Rearrangement of α-Alkoxy Esters
Podunavac, Ma?a,Lacharity, Jacob J.,Jones, Kerry E.,Zakarian, Armen
supporting information, p. 4867 - 4870 (2018/08/24)
A systematic investigation into the Ireland-Claisen rearrangement of α-alkoxy esters is reported. In all cases, the use of KN(SiMe3)2 in toluene gave rearrangement products corresponding to a Z-enolate intermediate with excellent diastereoselectivity, presumably because of chelation control. On the other hand, chelation-controlled enolate formation could be overcome for most substrates through the use of lithium diisopropylamide (LDA) in tetrahydrofuran (THF).
Chemoselective deoxygenation of ether-substituted alcohols and carbonyl compounds by B(C6F5)3-catalyzed reduction with (HMe2SiCH2)2
Yang, Wenyu,Gao, Lu,Lu, Ji,Song, Zhenlei
supporting information, p. 4834 - 4837 (2018/05/23)
B(C6F5)3-catalyzed deoxygenation of ether-substituted alcohols and carbonyl compounds has been developed using (HMe2SiCH2)2 as the reductant. This unique reagent shows distinct superiority over traditional one silicon-centered hydrosilanes, giving the corresponding alkanes in high yields with good tolerance of ethers, aryl halides and alkenes. The control experiments suggest that (HMe2SiCH2)2 might facilitate the approach in an intramolecular Si/O activation manner.
Dehydrogenative Synthesis of Linear α,β-Unsaturated Aldehydes with Oxygen at Room Temperature Enabled by tBuONO
Wang, Mei-Mei,Ning, Xiao-Shan,Qu, Jian-Ping,Kang, Yan-Biao
, p. 4000 - 4003 (2017/06/19)
Synthesis of linear α,β-unsaturated aldehydes via a room-temperature oxidative dehydrogenation has been realized by the cocatalysis of an organic nitrite and palladium with molecular oxygen as the sole clean oxidant. Linear α,β-unsaturated aldehydes could be efficiently prepared under aerobic catalytic conditions directly from the corresponding saturated linear aldehydes. Besides linear products, the aromatic analogy could also be smoothly achieved by the same standard method. The organic nitrite redox cocatalyst and alcohol solvent play a key role for realizing this method.
Oxidative Cleavage of Silyl Ethers by an Oxoammonium Salt
Loman, Jacob J.,Pistritto, Vincent A.,Kelly, Christopher B.,Leadbeater, Nicholas E.
supporting information, p. 2372 - 2377 (2016/09/28)
A method for the oxidative cleavage of silyl ethers to their corresponding carbonyl species mediated by an oxoammonium salt is described. The resulting aldehydes and ketones are obtained under mild reaction conditions with no observed overoxidation. For robust substrates, heating to reflux temperatures significantly reduces the reaction time.
Traceless Rhodium-Catalyzed Hydroacylation Using Alkyl Aldehydes: The Enantioselective Synthesis of β-Aryl Ketones
Bouisseau, Ana?s,Gao, Ming,Willis, Michael C.
supporting information, p. 15624 - 15628 (2016/10/25)
A one-pot three-step sequence involving Rh-catalyzed alkene hydroacylation, sulfide elimination and Rh-catalyzed aryl boronic acid conjugate addition gave products of traceless chelation-controlled hydroacylation employing alkyl aldehydes. The stereodefined β-aryl ketones were obtained in good yields with excellent control of enantioselectivity. Good variation of all three reaction components is possible.
Highly enantioselective copper(i)-catalyzed conjugate addition of 1,3-diynes to α,β-unsaturated trifluoromethyl ketones
Sanz-Marco, Amparo,Blay, Gonzalo,Mu?oz, M. Carmen,Pedro, José R.
supporting information, p. 8958 - 8961 (2015/05/27)
The conjugate diynylation of α,β-unsaturated trifluoromethyl ketones is carried out in the presence of a low catalytic load (2.5 mol%) of a copper(i)-MeOBIPHEP complex, triethylamine and a terminal 1,3-diyne. Pre-metalation of the terminal 1,3-diyne with stoichiometric or higher amounts of dialkylzinc reagent is not required. The corresponding internal diynes bearing a propargylic stereogenic center are obtained with good yields and excellent enantioselectivities. This journal is
Oxidative cleavage of allyl ethers by an oxoammonium salt
Kelly, Christopher B.,Ovian, John M.,Cywar, Robin M.,Gosselin, Taylor R.,Wiles, Rebecca J.,Leadbeater, Nicholas E.
, p. 4255 - 4259 (2015/04/14)
A method to oxidatively cleave allyl ethers to their corresponding aldehydes mediated by an oxoammonium salt is described. Using a biphasic solvent system and mild heating, cleavage proceeds readily, furnishing a variety of α,β-unsaturated aldehydes and ketones.
