24192-01-6Relevant academic research and scientific papers
Ni/Chiral Sodium Carboxylate Dual Catalyzed Asymmetric O-Propargylation
Chang, Xihao,Guo, Chang,Peng, Lingzi,Xu, Xianghong
, p. 21048 - 21055 (2021/12/14)
A highly enantioselective O-propargylation catalyzed by combining a phosphine-nickel complex and an axially chiral sodium dicarboxylate has been developed. The transformation features mild reaction conditions, a broad substrate scope, and excellent functional group tolerance, offering an efficient approach to an array of enantioenriched O-propargyl hydroxylamines. Mechanistic studies support the presumed role of the chiral carboxylate as a counterion for nickel catalysis enabling the discovery of highly stereoselective transformations. The power of this reaction is illustrated by its application in the asymmetric total synthesis of potent firefly luciferase inhibitors and (S)-dihydroyashabushiketol.
Chlorine, an atom economical auxiliary for asymmetric aldol reactions
Halperin, Shira D.,Britton, Robert
, p. 1702 - 1705 (2013/03/29)
An auxiliary strategy has been developed for asymmetric reactions of aldehydes in which the auxiliary itself is not chiral, but a single chlorine atom introduced via organocatalytic α-chlorination. The stereodirecting influence of the chlorine atom is then exploited prior to its removal by radical reduction. This strategy is demonstrated in the synthesis of several aldols (92-99% ee) and the natural products (+)-dihydroyashabushiketol and (+)-solistatin.
Total synthesis of (5S)-dihydroyashabushiketol
Romanski, Jan,Nowak, Piotr,Chapuis, Christian,Jurczak, Janusz
experimental part, p. 787 - 790 (2011/08/06)
Enantiomerically pure (+)-(5S)-dihydroyashabushiketol 1a was obtained by the 1,3-dipolar cycloaddition of a nitrile oxide, generated from oxime 3b, to N-acryloyl bornane[10,2]sultam (2R)-2 (67%, 85% de, then crystallization 81%, 99% de), followed by reduc
Synthesis and evaluation of estrogen agonism of diaryl 4,5- dihydroisoxazoles, 3-hydroxyketones, 3-methoxyketones, and 1,3-diketones: A compound set forming a 4D molecular library
Pulkkinen, Juha T.,Honkakoski, Paavo,Per?kyl?, Mikael,Berczi, Istvan,Laatikainen, Reino
supporting information; experimental part, p. 3562 - 3571 (2009/04/06)
In this paper, the preparation and systematic evaluation of estrogen receptor α (ERα) and estrogen receptor β (ERβ) activities of some diaryl-1,3-diones and their synthetic intermediates, diaryl-4,5-dihydroisoxazoles, diaryl-3-hydroxyketones, diaryl-3-met
Stereoselective crossed aldol reaction via boron enolates generated from α-iodo ketones and 9-borabicyclo[3.3.1]nonane
Mukaiyama, Teruaki,Takuwa, Tomofumi,Yamane, Keiko,Imachi, Shouhei
, p. 813 - 823 (2007/10/03)
Boron enolates were in situ-generated reductively by treating various α-iodo ketones such as 2-iodo-1-phenylpropan-1-one, 2-iodo-1-(4-methoxyphenyl)propan-1-one, 2-iodopentan-3-one, 2-iodo-2-methyl-1-phenylpropan-1-one, 3,4-dihydro-2-iodo-1(2H)-naphthalenone, 2-iodo-1-phenylethan-1-one and 1-iodo-4-phenylbutan-2-one with 9-borabicyclo[3.3.1]nonane (9-BBN). Aldols were produced in good yields with good to high diastereoselectivities by subsequent reaction of boron enolates thus formed with various aldehydes. Several boron enolates derived from α-iodo ketones and pinacolatoborane were successfully isolated by distillation, though the yields were rather moderate.
Synthesis and digestibility inhibition of diarylheptanoids: Structure- activity relationship
Bratt, Katharina,Sunnerheim, Kerstin
, p. 2703 - 2713 (2007/10/03)
(±)-5-Hydroxy-1,7-bis-(4'-hydroxyphenyl)-3-heptanone (2a), (±)5- hydroxyl-1-(4'-hydroxyphenyl)-7-phenyl-3-heptanone (2b), (±)-5-hydroxy-7- (4'-hydroxyphenyl)-1-phenyl-3-heptanone (2c), and (±)-5-hydroxy-1,7- bis(phenyl)-3-heptanone (2d) have been synthesized to study the structure- activity relationship regarding digestibility inhibition in vitro in cow rumen fluid. The activities were compared with the activity of chiral (S)-2a and its glucoside platyphylloside (1), isolated from Betula pendula. Compound 2a was slightly less active, 2b and 2c were more active, and 2d was less active than (S)-2a and platyphylloside.
Stereoselective Preparation of Acyclic syn-β-Amino Alcohols from β-Hydroxy Ketones via the Corresponding O-Benzyl Oximes
Narasaka, Koichi,Ukaji, Yutaka,Yamazaki, Shigeru
, p. 525 - 534 (2007/10/02)
Reduction of β-hydroxy ketone O-benzyl oximes with lithium aluminum hydride in the presence of sodium or potassium methoxide afforded the corresponding syn-β-amino alcohols in highly stereoselective manner.A lythraceae alkaloid, lasubine II, was synthesiz
NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 47. A GENERAL, EFFICIENT, AND CONVENIENT SYNTHESIS OF DIARYLHEPTANOIDS
Kato, Nobuharu,Hamada, Yasumasa,Shioiri, Takayuki
, p. 3323 - 3326 (2007/10/02)
An efficient synthesis of physiologically interesting diarylheptanoids has been carried out through direct C-acylation using diethyl phosphorocyanidate (DEPC) followed by Grignard reactions with aldehydes.Keywords - diarylheptanoid; C-acylation; diethyl p
Studies on the Constituents of the Seeds of Alpinia katsumadai Hayata
Kuroyanagi, Masanori,Noro, Tadataka,Fukushima, Seigo,Aiyama, Ritsuo,Ikuta, Akira,et al.
, p. 1544 - 1550 (2007/10/02)
Four new diarylheptanoids ha
