Diastereoselective Petasis Mannich reactions accelerated by hexafluoroisopropanol: a pyrrolidine-derived arylglycine synthesis |
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Authors: | Kausik K Nanda B Wesley Trotter |
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Institution: | Department of Medicinal Chemistry, Merck Research Laboratories, West Point, PA 19486, USA |
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Abstract: | A diastereoselective synthesis of pyrrolidine-derived arylglycines has been developed using the Petasis boronic acid Mannich reaction. High diastereoselectivities in the reactions of chiral amines, aryl boronic acids, and glyoxylic acid monohydrate have been demonstrated for the first time. Key to the implementation of this method is the discovery that hexafluoroisopropanol accelerates the Petasis process, reducing reaction times from multiple days to less than 24 h. |
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Keywords: | Petasis Boronic acid Mannich Arylglycine Diastereoselective |
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