55443-01-1Relevant academic research and scientific papers
Oxidative umpolung ?±-alkylation of ketones
Shneider, O. Svetlana,Pisarevsky, Evgeni,Fristrup, Peter,Szpilman, Alex M.
supporting information, p. 282 - 285 (2015/03/05)
We disclose a hypervalent iodine mediated ?±-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable to all common classes of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The ?±-alkylated carbonyl products are formed in up to 93% yield. An ionic mechanism is inferred based on meticulous analysis, NMR studies, trapping and crossover experiments, and computational studies.
OPSIN-BINDING LIGANDS, COMPOSITIONS AND METHODS OF USE
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Page/Page column 139-140, (2013/05/09)
Compounds are disclosed that are useful for treating ophthalmic conditions caused by or related to production of toxic visual cycle products that accumulate in the eye, such as dry adult macular degeneration, as well as conditions caused by or related to the misfolding of mutant opsin proteins and/or the mis-localization of opsin proteins. Compositions of these compounds alone or in combination with other therapeutic agents are also described, along with therapeutic methods of using such compounds and/or compositions. Methods of synthesizing such agents are also disclosed.
Photoinduced electron transfer promoted radical ring expansion and cyclization reactions of α-(ω-carboxyalkyl) β-keto esters
Nishikawa, Keisuke,Ando, Tomoki,Maeda, Kousuke,Morita, Toshio,Yoshimi, Yasuharu
supporting information, p. 636 - 638 (2013/04/10)
Photoinduced electron transfer (PET) promoted decarboxylation of α-(ω-carboxyalkyl) β-keto esters undergoes radical ring expansion and cyclization reactions. This mild and environmentally friendly method can provide one-carbon expanded γ-keto esters and b
Regioselective α-Alkylation of Extended Enolates Derived from Enamines of β-Keto Esters. Studies Relating to the Synthesis of 2-Substituted 2-Alkoxycarbonylcycloalkanones
Hodgson, Anne,Marshall, Joanne,Hallett, Peter,Gallagher, Timothy
, p. 2169 - 2174 (2007/10/02)
Enamines 4a-c, 5a-c and 6 have been prepared (from the corresponding 5-, 6- and 7-ring cyclic β-keto esters) and converted into enolates of general structure 2.These extended enolates react with alkyl halides at the α-site exclusively and the resulting adducts, exemplified by 7, have been hydrolysed to the corresponding 2-substituted 2-alkoxycarbonylcycloalkanones.These results are discussed in the context of the regioselectivity that has been reported for related enolates which tend, depending on the structure, to show a preference for γ-selectivity in their reactions with electrophiles.The asymmetric variant of the alkylation sequence described has also been examined but only modest enantioselectivity (up to 33percent e.e.) has been attained by incorporation of (S)-2-methoxymethylpyrrolidine 25, via enamine 26.Further progress was blocked by problems encountered in the synthesis of the requisite enamines when the more hindered C2-symmetric amines, such as (2R,5R)-2,5-dimethylpyrrolidine 27, were used, thereby limiting the more general synthetic utility and scope of this extended enolates.
The Synthesis of All of the Dimethyldibenzothiophenes and Monoethyldibenzothiophenes
Tedjamulia, Marvin L.,Tominaga, Yoshinori,Castle, Raymond N.
, p. 1485 - 1495 (2007/10/02)
The synthesis of all four isomers of the monoethyldibenzothiophenes and all of the sixteen isomers of the dimethyldibenzothiophenes has been accomplished.
