142301-75-5Relevant academic research and scientific papers
Streamlined Synthesis of C(sp3)-Rich N-Heterospirocycles Enabled by Visible-Light-Mediated Photocatalysis
Flodén, Nils J.,Trowbridge, Aaron,Willcox, Darren,Walton, Scarlett M.,Kim, Yongjoon,Gaunt, Matthew J.
supporting information, p. 8426 - 8430 (2019/06/13)
We report a general visible-light-mediated strategy that enables the construction of complex C(sp3)-rich N-heterospirocycles from feedstock aliphatic ketones and aldehydes with a broad selection of alkene-containing secondary amines. Key to the
Multifunctional 1,3-diphenylguanidine for the carboxylative cyclization of homopropargyl amines with CO2 under ambient temperature and pressure
Gao, Xiao-Tong,Xie, Shi-Liang,Zhou, Feng,Wu, Hai-Hong,Zhou, Jian
supporting information, p. 14303 - 14306 (2019/12/03)
Herein, we report that 1,3-diphenylguanidine (DPG) could be utilized for the carboxylative cyclization of homopropargyl amines with CO2 under ambient temperature and pressure, in combination with AgSbF6, which enabled the synthesis o
Synthesis of homopropargylamines from 2-cyanoazetidines
Quinodoz,Wright,Drouillat,David,Marrot,Couty
, p. 10072 - 10075 (2016/08/15)
2-Cyanoazetidines, easily accessible from β-amino alcohols, undergo ring-cleavage upon reaction with trimethylsilylazide and catalytic amounts of Bu2SnO, to give the corresponding homopropargylamines which are isolated as their N-Boc protected
Biogenetically inspired total syntheses of lycopodium alkaloids, (+)-flabellidine and (-)-lycodine
Azuma, Masayuki,Yoshikawa, Tetsuya,Kogure, Noriyuki,Kitajima, Mariko,Takayama, Hiromitsu
supporting information, p. 11618 - 11621 (2014/11/08)
The first asymmetric total synthesis of (+)-flabellidine (2) and the shortest total synthesis of (-)-lycodine (3) were accomplished by a strategy featuring the one-pot construction of a tetracyclic lycodine skeleton from a linear precursor, which was insp
Enantio- and diastereoselective palladium catalysed arylative and vinylative allene carbocyclisation cascades
Li, Meiling,Hawkins, Alison,Barber, David M.,Bultinck, Patrick,Herrebout, Wouter,Dixon, Darren J.
, p. 5265 - 5267 (2013/06/27)
The enantioselective synthesis of heavily decorated spirolactams has been accomplished via an arylative or vinylative allene carbocyclisation cascade. Mediated by silver phosphate, a range of allene-linked pro-nucleophiles and aryl or vinyl iodides were reacted in the presence of catalytic Pd(OAc)2 and chiral bis(oxazoline) ligands to afford the spirolactam products in good yields and high enantio- and diastereoselectivities. The Royal Society of Chemistry 2013.
Gold-catalyzed synthesis of alkylidene 2-oxazolidinones and 1,3-oxazin-2-ones
Robles-Machin, Rocio,Adrio, Javier,Carretero, Juan Carlos
, p. 5023 - 5026 (2007/10/03)
N-Boc-protected alkynylamines are converted into the corresponding alkylidene 2-oxazolidinones or 2-oxazinones under very mild reaction conditions in the presence of 1-5 mol % of a cationic Au(I) complex. The scope of the reaction is very general, providi
Heterocycles in Asymmetric Synthesis. Part 1. Construction of the Chiral Building Blocks for Enantioselective Alkaloid Synthesis via an Asymmetric Intramolecular Michael Reaction
Hirai, Yoshiro,Terada, Takashi,Yamazaki, Takao,Momose, Takefumi
, p. 509 - 516 (2007/10/02)
The asymmetric intramolecular Michael reaction of acyclic compounds ethyl (E)-4-but-2-enoate 9, and ethyl (E)-5-pent-2-enoate 10 was investigated under a variety of conditions, and the pyrrolidine ethyl (4-acetyl-1-benzylpyrrolidin-3-yl)acetate 11 and piperidine ethyl (3-acetyl-1-benzylpiperidin-4-yl)acetate 12, versatile chiral building blocks for alkaloid synthesis, were obtained in moderate to excellent optical yield.Cyclization of the aforementioned but- and pent-2-enoate using (R)-1-phenylethylamine in THF in the presence of molecular sieves 5 Angstroem gave the (+)-pyrrolidine derivative (+)-11 and the (-)-piperidine derivative (-)-12 in 60 and 90percent ee, respectively.When (S)-1-phenylethylamine was used, pyrrolidine (-)-11 and piperidine derivatives (+)-12 were obtained in similar optical yields, respectively.The ee of (-)- and (+)-piperidine derivatives increased up to 98percent upon recrystallization of their hydrobromid salts.
