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Synthesis of Acylborons by Ozonolysis of Alkenylboronates: Preparation of an Enantioenriched Amino Acid Acylboronate
Author(s) -
Taguchi Jumpei,
Ikeda Toshiki,
Takahashi Rina,
Sasaki Ikuo,
Ogasawara Yasushi,
Dairi Tohru,
Kato Naoya,
Yamamoto Yasunori,
Bode Jeffrey W.,
Ito Hajime
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201707933
Subject(s) - ozonolysis , amino acid , chemistry , oligopeptide , alanine , peptide , organic chemistry , potassium , peptide synthesis , aqueous solution , aqueous medium , combinatorial chemistry , stereochemistry , biochemistry
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.