190134-35-1Relevant academic research and scientific papers
Sustainable, mild and efficient p-methoxybenzyl ether deprotections utilizing catalytic DDQ
Walsh, Katie,Sneddon, Helen F.,Moody, Christopher J.
, p. 7380 - 7387 (2014)
A procedure for the selective deprotection of p-methoxybenzyl ethers using catalytic amounts of DDQ and of sodium nitrite, with oxygen as the terminal oxidant, is reported.
Silver(I)-Catalyzed deprotection of p -methoxybenzyl ethers: A mild and chemoselective method
Kern, Nicolas,Dombray, Thomas,Blanc, Aurelien,Weibel, Jean-Marc,Pale, Patrick
, p. 9227 - 9235,9 (2012/12/12)
The p-methoxybenzyl protecting group (PMB) on various alcohols and an acid was efficiently and selectively cleaved by the action of a catalytic amount of silver(I) hexafluoroantimonate combined with 0.5 equiv of 1,3,5- trimethoxybenzene in dichloromethane at 40 °C.
Synthesis of hexahydro-1H-benzo[c]chromen-1-amines via the intramolecular ring-opening reactions of aziridines by π-nucleophiles
Pulipaka, Aravinda B.,Bergmeier, Stephen C.
, p. 1420 - 1430 (2008/12/21)
The intramolecular cyclization of aziridines with π-nucleophiles can be a useful route to a number of heterocyclic and carbocyclic systems. This methodology has been applied to the synthesis of hexahydro-1H-benzo[c]chromen-1- amines, the basic skeleton of many amaryllidaceae alkaloids. The success of the aziridine cyclization is largely dependent on the N-substitution of aziridine, with activated aziridines not undergoing the cyclization reaction. Only N-H-, N-alkyl- and N-arylaziridines underwent the cyclization reaction. The ring opening of an unactivated aziridines with a π-nucleophile is one of the first examples of such a reaction. Georg Thieme Verlag Stuttgart.
Zeolite β-Induced Rearrangement of Alkoxybenzyl Allyl Ethers to Aldehydes and Ketones. 5.1 Variation of the Allylic Moiety
Wennerberg, Johan,Olofsson, Charlotte,Frejd, Torbjoern
, p. 3595 - 3598 (2007/10/03)
Allylic PMB ethers rearranged in the presence of zeolite β to form 4-arylbutanals or 5-arylpentanones depending on the substituent pattern of the allylic moiety. Best results were obtained with substrates carrying simple substituents in the allylic 2-posi
Dirhodium(II)-catalyzed intramolecular carbon-hydrogen insertion reaction of α-diazoketones: Synthesis of 7-silyloxyoctahydrobenzo[b]furan- 2-ones
Yakura, Takayuki,Yoshida, Daisaku,Ueki, Akiharu,Nakao, Keiko,Ikeda, Masazumi
, p. 651 - 658 (2007/10/03)
A dirhodium(II)-catalyzed intramolecular C-H insertion reaction of 2- oxygen-substituted cyclohexyl diazo-acetoacetates 1a-f was investigated. In contrast to the trans-2-methoxy- 1a and trans-2-(p-methoxybenzyloxy)- cyclohexyl derivatives lb, which upon treatment with 1 mol% dirhodium(II) tetraacetate in boiling benzene, gave a complex mixture, the trans-2-(tert- butyldimethylsilyloxy)cyclohexyl derivative 1c gave, in addition to the β- lactone 3c (16%), cis- and trans-fused octahydrobenzo[b]furan-2-ones 2c in 22 and 18% yields, respectively. Similar treatment of the cis-isomer 1d gave the β-lactone 3d as the major product (34%) and cis- and trans-fused γ,- lactones 2d (7 and 18% yields, respectively) as minor products. The (1R*,2R*,3R*)-3-benzyloxy-2-(tert-butyldimethyl-silyloxy)cyclohexyl derivative 1e gave the γ-lactones 2e in 75% combined yield as a 5:2 mixture of cis- and transfused isomers, while the (1R*,2S*,3R*)-isomer. If afforded the trans-fused γ-lactone 2f in 62% yield as a single product.
