Acceleration of Petasis Reactions of Salicylaldehyde Derivatives with Molecular Sieves
The Journal of Organic Chemistry2011Vol. 77(2), pp. 1154–1160
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Xianglin Shi, Dominique Hébrault, Michael Humora, William F. Kiesman, Hairuo Peng, Tina Talreja, Zezhou Wang, Zhili Xin
Abstract
Mild reaction conditions for Petasis reactions of substituted salicylaldehydes with various amines and arylboronic acids in the presence of molecular sieves were developed. Molecular sieves (MS) significantly accelerated the reaction rates and drove the reactions to high conversions. The conditions were applied to the synthesis of the core structure of BIIB042, a γ-secretase modulator, without stereochemical erosion of a stereogenic center in the salicylaldehyde intermediate.
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