103548-16-9Relevant academic research and scientific papers
A general synthesis of homochiral β-hydroxy N-acetylcysteamine thioesters
Le Sann, Christine,Simpson, Thomas J.,Smith, David I.,Watts, Paul,Willis, Christine L.
, p. 4093 - 4096 (1999)
A convenient and efficient route for the enantioselective synthesis of functionalised β-hydroxy N-acetylcysteamine thioesters is described. The route allows the facile incorporation of vicinal 13C labelling to produce intermediates required for biosynthetic studies on a wide range of polyketide metabolites, e.g. 6-MSA, monocerin, colletodiol and strobilurins.
Stereoselective synthesis of (S)-dapoxetine: A chiral auxiliary mediated approach
Khatik, Gopal L.,Sharma, Ratnesh,Kumar, Varun,Chouhan, Mangilal,Nair, Vipin A.
, p. 5991 - 5993 (2013)
An imidazolidin-2-one chiral auxiliary mediated acetate aldol reaction was explored in the enantioselective synthesis of (S)-dapoxetine (SSRI). The diastereoselective aldol adduct was transformed to highly enantiopure (S)-dapoxetine with overall good yield.
Directed Asymmetric Reduction of a Carbonyl Group via a New Homochiral Boronate Ester
Mears, Richard J.,Whiting, Andrew
, p. 8155 - 8156 (1993)
Homochiral β-boronate carbonyl derivative 4 directs the asymmetric reduction of the ketone moiety, providing 89percent enantiomeric excess of the (S)-diol 6, using borane-tetrahydrofuran as the reducing agent.
Lewis base activation of Lewis acids: Vinylogous aldol additions of silyl dienol ethers to aldehydes
Denmark, Scott E.,Heemstra Jr., John R.
, p. 2411 - 2416 (2004)
Highly regioselective vinylogous aldol additions of silyl dienol ethers derived from simple α,β-unsaturated ketones are described. The catalyst system of silicon tetrachloride activated by chiral bisphosphoramide (R,R)-1 effectively promotes the addition
Asymmetric catalysis. Asymmetric catalytic intramolecular hydrosilation and hydroacylation
Barnhart, Richard W.,Wang, Xianqi,Noheda, Pedro,Bergens, Steven H.,Whelan, John,Bosnich
, p. 4335 - 4346 (1994)
Catalysts of the type [Rh(chiral diphosphine)]+ efficiently catalyse the intramolecular hydrosilation of silyl ethers derived from allylic alcohols. The products can be converted to chiral 1,3-diols. High enantiomeric excesses (ee's) are observ
Copper(I)-Catalyzed Asymmetric Vinylogous Aldol-Type Reaction of Allylazaarenes
Wang, Si-Qing,Liu, Zong-Ci,Yue, Wen-Jun,Yin, Liang
, p. 4604 - 4608 (2021)
A vinylogous aldol-type reaction of allylazaarenes and aldehydes is disclosed that affords a series of chiral γ-hydroxyl-α,β-unsaturated azaarenes in moderate to excellent yields with high to excellent regio- and enantioselectivities. With (R,RP)-TANIAPHOS and (R,R)-QUINOXP* as the ligand, the carbon-carbon double bond in the products is generated in (E)-form. With (R)-DTBM-SEGPHOS as the ligand, (Z)-form carbon-carbon double bond is formed in the major product. In this vinylogous reaction, aromatic, α,β-unsaturated, and aliphatic aldehydes are competent substrates. Moreover, a variety of azaarenes, such as pyrimidine, pyridine, pyrazine, quinoline, quinoxaline, quinazoline, and benzo[d]imidazole are well-tolerated. At last, the chiral vinylogous product is demonstrated as a suitable Michael acceptor towards CuI-catalyzed nucleophilic addition with organomagnesium reagents.
Enantioselective synthesis of (+)-sedamine and (-)-allosedamine
Yadav,Reddy, M. Sridhar,Rao, P. Purushothama,Prasad
, p. 4005 - 4012 (2006)
Two different approaches to the enantioselective syntheses of (+)-sedamine and (-)-allosedamine are described, both using the Sharpless asymmetric epoxidation as the key step. Regioselective reduction of epoxides, chemoselective oxidation of alcohols, ring-closing metathesis, and nucleophilic displacements were the other key steps employed. Georg Thieme Verlag Stuttgart.
Purification and characterization of a (r)-1-phenyl-1, 3-propanediol- producing enzyme from trichosporon fermentans aj-5152 and enzymatic (r)-1-phenyl-1, 3-propanediol production
Kira, Ikuo,Onishi, Norimasa
, p. 1640 - 1646 (2009)
An (R)-1-phenyl-1, 3-propanediol-producing enzyme was purified from Trichosporon fermentans AJ-5152. It was NADPH-dependent and converted 3-hydroxy-1- phenylpropane-1-one (HPPO) to (R)-1-phenyl-1, 3-propanediol [(R)-PPD] with anti-Prelog's specificity. It
A site isolation-enabled organocatalytic approach to enantiopure γ-amino alcohol drugs
Wang, Shoulei,Rodríguez-Escrich, Carles,Fan, Xinyuan,Pericàs, Miquel A.
, p. 3943 - 3946 (2018)
Solid support-enabled site isolation has previously allowed to use paraldehyde as an acetaldehyde surrogate in aldol reactions. However, only electron-poor aldehydes were tolerated by the system. Herein, we show that the temporary conversion of benzaldehyde into η6-benzaldehyde Cr(CO)3 circumvents this limitation. Asymmetric synthesis of (R)-Phenoperidine, as well as formal syntheses of (R)-Fluoxetine and (R)-Atomoxetine, illustrate the benefits of this strategy.
Catalyst-Directed Diastereo- and Site-Selectivity in Successive Nucleophilic and Electrophilic Allylations of Chiral 1,3-Diols: Protecting-Group-Free Synthesis of Substituted Pyrans
Shin, Inji,Wang, Gang,Krische, Michael J.
, p. 13382 - 13389 (2014)
The iridium-catalyzed, protecting group-free synthesis of 4-hydroxy-2,6-cis- or trans-pyrans through successive nucleophilic and electrophilic allylations of chiral 1,3-diols occurs with complete levels of catalyst-directed diastereoselectivity in the absence of protecting groups, premetallated reagents, or discrete alcohol-to-aldehyde redox reactions.
