Sequential Norrish Type II Photoelimination and Intramolecular Aldol Cyclization of 1,2‐Diketones in Carbohydrate Systems: Stereoselective Synthesis of Cyclopentitols

Álvarez-Dorta, Dimitri; León, Elisa I.; Kennedy, Alan R.; Riesco‐Fagundo, Concepción; Suárez, Ernesto

doi:10.1002/anie.200803696

Cited by 31 publications

(11 citation statements)

References 45 publications

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“…Because the yield is quantitative, the privileged conformation in the photochemically excited substrate favors the hydrogen abstraction step. The conformation equilibrium in the diradical intermediate 106 is also favorable for the cyclization . This is not always the case.…”

Section: Photochemically Induced Hydrogen Transfer In Different Waysmentioning

confidence: 99%

Electron and hydrogen transfer in organic photochemical reactions

Hoffmann

2014

J of Physical Organic Chem

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Electron and hydrogen transfers are basic steps in many chemical reactions. Photochemical or electronic excitation significantly influences the reactivity of chemical compounds and thus also these transfer processes. Furthermore, the formation of typical intermediates has a decisive impact on the outcome of the transformations. Based on these properties of photochemical processes, efficient homogeneous and heterogeneous photocatalytic transformations for application to organic synthesis have been developed. Efficient reactions without any chemical activation but induced by photochemical electron transfer can also be carried out. The photon acts as a traceless reagent. In the context of photochemical hydrogen transfer, two processes are frequently encountered. The two particles the electron and the proton are transferred either simultaneously or in two steps. In the latter case, the electron is transferred first and the proton follows. Both processes are applied to organic synthesis. Copyright © 2014 John Wiley & Sons, Ltd.

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Section: Photochemically Induced Hydrogen Transfer In Different Waysmentioning

confidence: 99%

Electron and hydrogen transfer in organic photochemical reactions

Hoffmann

2014

J of Physical Organic Chem

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“…C -Acyl glycosides are versatile synthetic intermediates to natural products, nucleoside analogues, and pharmaceutical molecules ( Scheme 1A ). 1 Downstream derivatives of C -acyl glycosides, including C -alkyl glycosides, 2 diazo derivatives, 3 alcohols, 4 nucleoside analogues, 5 and cyclopentitols, 6 display significant potentials in drug discovery and utilities in chemical biology and biochemistry studies. A C -glycoside linkage confers in vivo stability towards hydrolysis and enzymatic degradation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of C-acyl furanosides via the cross-coupling of glycosyl esters with carboxylic acids

2021

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“…When the diketone moiety is placed in the former anomeric position of the glucose derivative 24, a Norrish type II reaction takes place. 27 Scheme 5. Regio and stereoselective hydrogen abstraction followed by radical cyclization in -unsaturated lactones.…”

Section: Introductionmentioning

confidence: 99%

Studies in organic and physical photochemistry – an interdisciplinary approach

Oelgemöller

Hoffmann

2016

Org. Biomol. Chem.

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Traditionally, organic photochemistry when applied to synthesis strongly interacts with physical chemistry. The aim of this review is to illustrate this very fruitful interdisciplinary approach and cooperation. A profound understanding of the photochemical reactivity and reaction mechanisms is particularly helpful for optimization and application of these reactions. Some typical reactions and particular aspects are reported such as the Norrish-Type II reaction and the Yang cyclization and related transformations, the [2 + 2] photocycloadditions, particularly the Paternò-Büchi reaction, photochemical electron transfer induced transformations, different kinds of catalytic reactions such as photoredox catalysis for organic synthesis and photooxygenation are discussed. Particular aspects such as the structure and reactivity of aryl cations, photochemical reactions in the crystalline state, chiral memory, different mechanisms of hydrogen transfer in photochemical reactions or fundamental aspects of stereoselectivity are discussed. Photochemical reactions are also investigated in the context of chemical engineering. Particularly, continuous flow reactors are of interest. Novel reactor systems are developed and modeling of photochemical transformations and different reactors play a key role in such studies. This research domain builds a bridge between fundamental studies of organic photochemical reactions and their industrial application.

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Sequential Norrish Type II Photoelimination and Intramolecular Aldol Cyclization of 1,2‐Diketones in Carbohydrate Systems: Stereoselective Synthesis of Cyclopentitols

Cited by 31 publications

References 45 publications

Electron and hydrogen transfer in organic photochemical reactions

Electron and hydrogen transfer in organic photochemical reactions

Synthesis of C-acyl furanosides via the cross-coupling of glycosyl esters with carboxylic acids

Studies in organic and physical photochemistry – an interdisciplinary approach

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