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Asymmetric synthesis of orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithine

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Catalytic Enantioselective Synthesis of Inherently Chiral Macrocycles by Dynamic Kinetic Resolution

Jieping Zhu, Shuo Tong

Kinetically fast racemization of chiral substrates through an achiral intermediate and enantioselective functionalization of one of the enantiomeric substrates forms the basis of the dynamic kinetic resolution (DKR) of centrally chiral molecules. We report ...

2024

In summary, the development of the catalytically formed chiral auxiliary concept is described. In this approach, an oxazolidine auxiliary is installed via enantioselective Pd catalysis from readily available starting materials in an enantioselective tether ...

EPFL2023

An asymmetric 3-component reaction between EthynylBenziodoXoles (EBXs), 2,2,2-trifluorodiazoethane and nucleophiles catalyzed by a CuI-BOX (Bisoxazoline) catalyst is described. This protocol gives access to chiral trifluoromethylated propargyl ethers and a ...

2023

The first chapter of this thesis describe the development of a general synthesis of ynimines, an under-exploited motif in organic chemistry. In the presence of an inexpensive copper catalyst and 2,2'-biquinoline, reaction of easily accessible O-acyloximes ...

EPFL2023

Enantioselective Total Synthesis of (+)-Stephadiamine

Qian Wang, Jieping Zhu, Baochao Yang, Guang Li

An asymmetric synthesis of (+)-stephadiamine has been accomplished featuring (a) an enantioselective dearomatizative Michael addition to generate a quaternary stereocenter; (b) a domino sequence involving reductive generation of nitrone from γ-nitro ketone ...

2023

Asymmetric Cyclopropanation and Epoxidation via a Catalytically Formed Chiral Auxiliary

Jérôme Waser, Mikus Purins

For the enantioselective diversification of a single starting material, a different chiral catalyst is usually required for each transformation. Herein, we extend the concept of catalytically formed chiral auxiliary from hydrogenation to the asymmetric cyc ...

WILEY-V C H VERLAG GMBH2022

Enantio- and diastereoselective construction of vicinal C(sp(3)) centres via nickel-catalysed hydroalkylation of alkenes

Xile Hu, Chao Fan, Srikrishna Bera

In drug discovery, the proportion of aliphatic carbons (C(sp(3))) and the presence of chiral carbons in organic molecules are positively correlated to their chance of clinical success. Although methods exist for the synthesis of chiral C(sp(3))-rich molecu ...

NATURE PORTFOLIO2022

Deracemization of racemic chiral compounds is an attractive approach in asymmetric synthesis, but its development has been hindered by energetic and kinetic challenges. Here we describe a catalytic deracemization method for secondary benzylic alcohols whic ...

WILEY-V C H VERLAG GMBH2021

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We report herein the enantioselective total synthesis of three monoterpene indole alkaloids, namely, (+)-alstilobanine C, (+)-undulifoline, and (-)-alpneumine H. The key features of our synthesis include: a) introduction of chirality via enantioselective d ...

WILEY-V C H VERLAG GMBH2021

1,2-Bis(2'-nitrophenoxy)-3-R-benzenes {R = H (1), CH3 (2) and OCH3 (3)} have been prepared from the S-N-Ar reaction between 1-fluoro-2-nitrobenzene and 3-R-catechol (aromatic diol), and are then reduced to the corresponding diamines 1,2-bis(2'-aminophenoxy ...

ROYAL SOC CHEMISTRY2021