103548-16-9Relevant articles and documents
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.
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.
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
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.
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.
Enantioselective β-hydroxy thioesters formation via decarboxylative aldol reactions of malonic acid half thioesters with aldehydes promoted by chloramphenicol derived sulfonamides
Wang, Yafeng,Huang, Guanxin,Hu, Sha,Jin, Kaijun,Wu, Yan,Chen, Fener
, p. 5055 - 5062 (2017)
A highly enantioselective synthesis of chiral β-hydroxy thioesters that uses a decarboxylative aldol reaction of malonic acid half thioesters and aldehydes catalyzed by a chloramphenicol base-derived bifunctional organocatalyst is reported. The resulting
Direct Deamination of Primary Amines via Isodiazene Intermediates
Berger, Kathleen J.,Driscoll, Julia L.,Yuan, Mingbin,Dherange, Balu D.,Gutierrez, Osvaldo,Levin, Mark D.
supporting information, p. 17366 - 17373 (2021/11/04)
We report here a reaction that selectively deaminates primary amines and anilines under mild conditions and with remarkable functional group tolerance including a range of pharmaceutical compounds, amino acids, amino sugars, and natural products. An anomeric amide reagent is uniquely capable of facilitating the reaction through the intermediacy of an unprecedented monosubstituted isodiazene intermediate. In addition to dramatically simplifying deamination compared to existing protocols, our approach enables strategic applications of iminium and amine-directed chemistries as traceless methods. Mechanistic and computational studies support the intermedicacy of a primary isodiazene which exhibits an unexpected divergence from previously studied secondary isodiazenes, leading to cage-escaping, free radical species that engage in a chain, hydrogen-atom transfer process involving aliphatic and diazenyl radical intermediates.