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
The Catalytic Asymmetric Intermolecular Prins Reaction
Diáz-Oviedo, C. David,Maji, Rajat,List, Benjamin
supporting information, p. 20598 - 20604 (2021/12/14)
Despite their significant potential, catalytic asymmetric reactions of olefins with formaldehyde are rare and metal-free approaches have not been previously disclosed. Here we describe an enantioselective intermolecular Prins reaction of styrenes and paraformaldehyde to form 1,3-dioxanes, using confined imino-imidodiphosphate (iIDP) Br?nsted acid catalysts. Isotope labeling experiments and computations suggest a concerted, highly asynchronous addition of an acid-activated formaldehyde oligomer to the olefin. The enantioenriched 1,3-dioxanes can be transformed into the corresponding optically active 1,3-diols, which are valuable synthetic building blocks.
Chiral Ion-Pair Organocatalyst-Promoted Efficient Enantio-selective Reduction of α-Hydroxy Ketones
Zhang, Yiliang,He, Li,Shi, Lei
, p. 1926 - 1931 (2018/03/27)
The enantioselective reduction of α-hydroxy ketones with catecholborane has been developed employing 5 mol% of an 1,1′-bi-2-naphthol (BINOL)-derived ion-pair organocatalyst. This methodology provides a straightforward access to the corresponding aromatic 1,2-diols in high yields (up to 90%) with excellent enantioselectivities (up to 97%). Furthermore, the α-amino ketones also could be reduced with moderate ee values under mild reaction condition. (Figure presented.).
