73234-87-4Relevant academic research and scientific papers
The Coming of Age in Iodane-Guided ortho-C?H Propargylation: From Insight to Synthetic Potential
Izquierdo, Susana,Bouvet, Sébastien,Wu, Yichen,Molina, Sonia,Shafir, Alexandr
supporting information, p. 15517 - 15521 (2018/10/02)
As early as 1991 Ochiai et al. reported that an acid-activated form of phenyliodine diacetate, PhI(OAc)2, undergoes a reaction with propargyl-silanes, germanes and stannanes to give the ortho-propargyl iodobenzene. This formal C?H alkylation wa
Synthesis of allenes via Nickel-catalyzed cross-coupling reaction of propargylic bromides with grignard reagents
Li, Qinghan,Gau, Hanmou
experimental part, p. 747 - 750 (2012/06/29)
We describe a convenient method for the synthesis of terminal allenes from cross-coupling of propargylic bromide with Grignard reagent. The reaction of propargylic bromide with 1.2 equivalents of Grignard reagent mediated by Ni(acac)2 (2 mol%) and Ph3P (4 mol%) in THF may produce terminal allenes in good yields and high regioselectivities at room temperature. Georg Thieme Verlag Stuttgart · New York.
Ipso Selectivity in the Reductive Iodonio-Claisen Rearrangement of Allenyl(p-methoxyaryl)iodinanes
Ochiai, Masahito,Ito, Takao,Masaki, Yukio
, p. 15 - 16 (2007/10/02)
Allenyl(aryl)iodinanes, generated from p-methoxy(diacetoxyiodo)arenes by the reaction with propyn-2-yl(trimethyl)silanes in the presence of BF3-Et2O in dichloromethane, undergo reductive ipso iodonio-Claisen rearrangement selectively at -20 deg C yielding
Synthetic Approach to Aklavinone Using 2-Oxo-2H-pyran-5-carboxylate (Coumalate) Intermediates
Jung, Michael E.,Hagenah, Jeffrey A.
, p. 1889 - 1902 (2007/10/02)
A novel approach for the preparation of aklavinone 5 is described in which the key step is the cycloaddition of a substituted coumalate with a ketene acetal to produce a masked A ring with the C and D rings attached.The 4-(arylmethyl)coumalate 53 was prepared from naphthalene-1,5-diol (6) by a seven step route involving as the key step the cyclocondensation of the methyl (arylmethyl)propiolate 52 with methyl 3-oxopentanoate 10.Cycloaddition of 53 with dimethyl ketene acetal 12 produced the potential A-ring precursor 67, which could not be cleanly reduced, thereby ending this scheme.The preparation of functionalized 4,6-dialkylpyrone-5-carboxylates and their use in the synthesis of bicyclic lactones and substituted benzoates via cycloaddition reactions are also described.
