期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 41, 页码 12659-12663出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201605754
关键词
boron; NMR spectroscopy; peptidomimetics; reaction kinetics; tautomerism
资金
- Canadian Foundation for Innovation [19119]
- Ontario Research Fund
- Natural Science and Engineering Research Council (NSERC)
- Canadian Institutes of Health Research (CIHR)
Herein, we demonstrate the use of -boryl aldehydes and acyl boronates in the synthesis of aminoboronic acid derivatives. This work highlights the untapped potential of boron-substituted iminium ions and offers insights into the behavior of N-methyliminodiacetyl (MIDA) boronates during condensation and tautomerization processes. The preparative value of this contribution lies in the demonstration that various amines, including linear and cyclic peptides, can be readily conjugated with boron-containing fragments. A mild deprotection of amino MIDA-boronates enables access to - and -aminoboronic acids in high chemical yields. This simple process should be applicable to the synthesis of a wide range of bioactive molecules as well as precursors for cross-coupling reactions.
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