4 years ago

Synthesis of Acylborons by Ozonolysis of Alkenylboronates: Preparation of an Enantioenriched Amino Acid Acylboronate

Synthesis of Acylborons by Ozonolysis of Alkenylboronates: Preparation of an Enantioenriched Amino Acid Acylboronate
Yasushi Ogasawara, Toshiki Ikeda, Ikuo Sasaki, Jumpei Taguchi, Yasunori Yamamoto, Hajime Ito, Jeffrey W. Bode, Naoya Kato, Tohru Dairi, Rina Takahashi
A concise synthesis of acylborons was achieved by ozonolysis of alkenyl MIDA (N-methyliminodiacetic acid) boronates. This reaction exhibits excellent functional-group tolerance and is applicable to various acyl MIDA boronates and potassium acyltrifluroborates (KATs) which could not be synthesized by previous methods. In addition, α-amino acylborons, which would be essential for peptide ligations, were prepared for the first time. The acylboron of l-alanine was obtained in high enantiopurity and found to be configurationally stable. Oligopeptide synthesis between the α-amino KATs and amino acid in dilute aqueous media was studied. In the (o)zone: Highly functionalized acylborons are prepared by ozonolysis of alkenyl MIDA boronates. The first synthesis of α-amino acylborons, including the enantiopure alanine-type acylboron was achieved by using this method. The products are essential for protein–protein conjugation by potassium acyltrifluoroborate ligation. Oligopeptide synthesis using α-amino acylborons proceeded in dilute aqueous medium and the alanine-type acylboron is configurationally stable under ligation conditions.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201707933

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