Copper-Catalyzed Stereoselective Synthesis of 2-Deoxygalactosides

Dong, Youxian; Yuma, Madina; Mei, Yuling; Jiang, Nan; Yang, Guofang; Wang, Zhongfu; Zhang, Jianbo

doi:10.1055/s-0040-1707098

Synlett

2020

DOI: 10.1055/s-0040-1707098

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Copper-Catalyzed Stereoselective Synthesis of 2-Deoxygalactosides

Youxian Dong

Madina Yuma

Yuling Mei

et al.

Abstract: An efficient glycosylation method to synthesize 2-deoxy-O-galactosides based on a Cu(II)-catalyzed reaction without additional ligand has been developed. The glycosylation was amenable to different protected glycal donors and a wide range of acceptors including alcohols, amino acids, sugars, and phenol, and proceeds with excellent yield and high α-selectivity under mild conditions. The reaction proceeds readily on a gram scale, and its versatility is exemplified in the synthesis of oligosaccharides.

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Cited by 4 publications

References 13 publications

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The Synthesis of Chiral Allyl Carbamates via Merger of Photoredox and Nickel Catalysis

Garbacz

Stecko

2020

Adv Synth Catal

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A mild, and versatile, organophotoredox/Ni‐mediated protocol was developed for the direct preparation of diverse, enantioenriched allyl carbamates. The reported approach represents a significant departure from classical step‐by‐step synthesis of allyl carbamates. This dual photoredox/Ni based strategy offers unrivalled capacity for convergent unification of readily available alkyl halides and chiral carbamates derived from 1‐bromo‐alken‐3‐ols with high chemoselectivity and efficiency. The reported photoredox/Ni catalyzed cross‐coupling reaction is not limited to carbamates, but also to other O‐derivatives such as esters, ethers, acetals, carbonates or silyl ethers. To demonstrate the utility of the reported protocol, the resulting allyl carbamates were transformed into functionalized non‐racemic allylamines through a sigmatropic rearrangement reaction in enantiospecific manner. This approach allowed for synthesis of enantiomeric allylamines by a simple control of the geometry of a double bond of allyl carbamates.magnified image

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The Synthesis of Chiral Allyl Carbamates via Merger of Photoredox and Nickel Catalysis

Garbacz

Stecko

2020

Adv Synth Catal

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Anion‐Bridged Dual Hydrogen Bond Enabled Concerted Addition of Phenol to Glycal

Jiao,

Guo,

Zheng

et al. 2024

Advanced Science

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A noncovalent organocatalytic concerted addition of phenol to glycal is developed for the stereoselective and regioselective construction of biologically important phenolic 2‐deoxyglycosides, featuring wide substrate tolerance. The method relies on an anion‐bridged dual hydrogen bond interaction which is experimentally proved by Nuclear Magnetic Resonance (NMR), Ultraviolet and visible (UV–vis), and fluorescence analysis. Experimental evidence including kinetic analysis, Kinetic Isotope Effect (KIE) studies, linear free energy relationship, Hammett plot, and density functional theory (DFT) calculations is provided for a concerted mechanism where a high‐energy oxocarbenium ion is not formed. In addition, the potential utility of this method is further demonstrated by the synthesis of biologically active glycosylated flavones. The benchmarking studies demonstrate significant advances in this newly developed method compared to previous approaches.

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A General Strategy for the Stereoselective Synthesis of Pyrrole‐Fused Chiral Skeletons: [3+2] Cycloaddition with 2‐Nitro‐2,3‐Unsaturated Glycosides

et al. 2021

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In this study, a two-step methodology was developed for the synthesis of chiral pyrroles from 2-nitroglycals via Ferrier rearrangement and Barton-Zard reaction under mild conditions without transition metal catalysts. The Ferrier rearrangement reaction of 2-nitro-glycals and a series of O-nucleophiles proceeded smoothly in the presence of N-heterocyclic carbene (NHC) catalyst and K 2 CO 3 which allowed the highly stereoselective synthesis of the diverse 2-nitro-2,3-unsaturated glyco-sides in excellent yields. Subsequently, the rearrangement products were conveniently transformed into the desired chiral pyrroles by [3 + 2] cycloaddition (Barton-Zard reaction) with isocyanoacetate in the presence of Cs 2 CO 3 . One-pot strategy was also successfully demonstrated for the gram-scale synthesis of one chiral pyrrole. This is the first report of stereoselective conversion from 2-nitroglycals to chiral pyrrole.

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Copper-Catalyzed Stereoselective Synthesis of 2-Deoxygalactosides

Cited by 4 publications

References 13 publications

The Synthesis of Chiral Allyl Carbamates via Merger of Photoredox and Nickel Catalysis

The Synthesis of Chiral Allyl Carbamates via Merger of Photoredox and Nickel Catalysis

Anion‐Bridged Dual Hydrogen Bond Enabled Concerted Addition of Phenol to Glycal

A General Strategy for the Stereoselective Synthesis of Pyrrole‐Fused Chiral Skeletons: [3+2] Cycloaddition with 2‐Nitro‐2,3‐Unsaturated Glycosides

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