Photolabile Protecting Groups in Organic Synthesis

Authored by: Christian G. Bochet , Aurélien Blanc

CRC Handbook of Organic Photochemistry and Photobiology

Print publication date:  March  2012
Online publication date:  March  2012

Print ISBN: 9781439899335
eBook ISBN: 9781466561250
Adobe ISBN:

10.1201/b12252-5

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Abstract

It is well known that, for the time being, certain functional groups need a temporary inactivation of their intrinsic chemical properties in order to allow transformations elsewhere in a molecule. This inactivation is achieved by protecting groups, the use of which has been frequently reviewed, commented, and criticized. 1,2 When the original reactivity of a functional group has to be restored, the protecting group needs to be removed by a reagent, which should be strong enough to induce the detachment of the protecting moiety, but mild enough to keep the rest of the molecule intact—including possibly other protecting groups that must be maintained for further transformations. This compatibility between different protecting groups, that is, the possibility of their selective removal in any given sequence, is often called orthogonality, and this is highly desirable in order to give to the synthetic plan a certain flexibility. However, the number of orthogonal sets of hydrolysis conditions is unfortunately rather small (e.g., acidic, basic, reductive, oxidizing, and nucleophilic conditions), and thus any additional dimension would be welcome.

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