Rapid Assessment of Protecting-Group Stability by Using a Robustness Screen

An experimentally simple method has been developed to rapidly establish the stability of widely utilized silyl, acetal, and carbamate protecting groups to a given set of reaction conditions. Assessment of up to twelve protecting groups in a single experiment has been demonstrated. Evaluation of this...

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Bibliographic Details
Published in:Chemistry : a European journal 2014-03, Vol.20 (13), p.3800-3805
Main Authors: Collins, Karl D., Rühling, Andreas, Lied, Fabian, Glorius, Frank
Format: Article
Language:English
Subjects:
arylation
Assessments
Chemistry
heterocycles
high-throughput screening
protecting groups
Robustness
robustness screen
Screens
Stability
Transformations
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Summary:An experimentally simple method has been developed to rapidly establish the stability of widely utilized silyl, acetal, and carbamate protecting groups to a given set of reaction conditions. Assessment of up to twelve protecting groups in a single experiment has been demonstrated. Evaluation of this protocol in two unrelated synthetic transformations suggests that this method can be used to select appropriate protecting groups in the design of synthetic routes. Stable or not? An experimentally simple method has been developed to rapidly establish the stability of widely utilized silyl, acetal, and carbamate protecting groups to a given set of reaction conditions (see figure; Ac=acetyl, Boc=tert‐butoxycarbonyl, TBS=tert‐butyldimetylsilyl). Assessment of up to twelve protecting groups in a single experiment has been demonstrated. This method could be used to select appropriate protecting groups in the design of synthetic routes.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201304508