European Journal of Organic Chemistry p. 1475 - 1478 (2017)
Update date:2022-08-28
Topics:
Poulie, Christian B. M.
Bunch, Lennart
Protection of α-amino acids with 9-borabicyclo[3.3.1]nonane (9-BBN) to give their corresponding boroxazolidones is highly attractive, as it concurrently masks both the amino and the carboxylic acid functionalities. However, the harsh methods required for deprotection of these boroxazolidones have limited their use. Herein, we report that tetrabutylammonium fluoride serves as a mild and versatile reagent that can be used to cleave boroxazolidones to their corresponding free α-amino acids. The reaction conditions were explored, including the use of various nucleophilic fluoride sources, solvents, and reaction temperatures. Nucleophilic fluoride sources comprising an ammonium cation proved superior to other countercations. The scope of the reaction was extended to the cleavage of B,B-diphenyl- and B,B-diethyl boroxazolidone complexes. Furthermore, a wide range of α-amino acid side-chain functionalities were shown to be compatible, including acids, esters, amides, thiols, thioethers, alkynes, phenols, basic heterocycles, and important biorelevant molecules such as glutathione, (S)-adenosyl-l-homocysteine, and l-biocytin.
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