3-Amino-1

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Seth B Herzon - One of the best experts on this subject based on the ideXlab platform.

  • general method for the synthesis of α or β deoxyaminoglycosides bearing basic nitrogen
    Journal of the American Chemical Society, 2021
    Co-Authors: Kevin M Hoang, Nicholas R Lees, Seth B Herzon
    Abstract:

    The introduction of glycosides bearing basic nitrogen is challenging using conventional Lewis acid-promoted pathways owing to competitive coordination of the amine to the Lewis acid promoter. Additionally, because many aminoglycosides lack a C2 substituent, diastereomeric mixtures of O-glycosides are often produced. Herein, we present a method for the synthesis of α- or β- 2,3,6-trideoxy-3-amino- and 2,4,6-trideoxy-4-amino O-glycosides from a common precursor. Our strategy proceeds by the reductive lithiation of thiophenyl glycoside donors and trapping of the resulting anomeric anions with 2-methyltetrahydropyranyl peroxides. We apply this strategy to the synthesis of α- and β-forosamine, pyrrolosamine, acosamine, and ristosamine derivatives using primary and secondary peroxides as electrophiles. α-Linked products are obtained in 60-96% yield and with >50:1 selectivity. β-Linked products are obtained in 45-94% yield and with 1.7->50:1 stereoselectivity. Contrary to donors bearing an equatorial amine substituent, donors bearing an axial amine substituent favored β-products at low temperatures. This work establishes a general strategy to synthesize O-glycosides bearing a basic nitrogen.

  • synthesis of 1 3 amino alcohols 1 3 diols amines and carboxylic acids from terminal alkynes
    ChemInform, 2015
    Co-Authors: Mingshuo Zeng, Seth B Herzon
    Abstract:

    Anti-Markovnikov functionalization reactions of terminal alkynes and propargylic amines efficiently lead to 1,3-diol products and 1,3-amino alcohols, respectively, without loss of stereochemistry.

  • synthesis of 1 3 amino alcohols 1 3 diols amines and carboxylic acids from terminal alkynes
    Journal of Organic Chemistry, 2015
    Co-Authors: Mingshuo Zeng, Seth B Herzon
    Abstract:

    The half-sandwich ruthenium complexes 1–3 activate terminal alkynes toward anti-Markovnikov hydration and reductive hydration under mild conditions. These reactions are believed to proceed via addition of water to metal vinylidene intermediates (4). The functionalization of propargylic alcohols by metal vinylidene pathways is challenging owing to decomposition of the starting material and catalytic intermediates. Here we show that catalyst 2 can be employed to convert propargylic alcohols to 1,3-diols in high yield and with retention of stereochemistry at the propargylic position. The method is also amenable to propargylic amine derivatives, thereby establishing a route to enantioenriched 1,3-amino alcohol products. We also report the development of formal anti-Markovnikov reductive amination and oxidative hydration reactions to access linear amines and carboxylic acids, respectively, from terminal alkynes. This chemistry expands the scope of products that can be prepared from terminal alkynes by practica...

Rosario M Diaz - One of the best experts on this subject based on the ideXlab platform.

Pinaki Talukdar - One of the best experts on this subject based on the ideXlab platform.

Estrella Álvarez - One of the best experts on this subject based on the ideXlab platform.

Humberto Rodriguezsolla - One of the best experts on this subject based on the ideXlab platform.