Amidoboronates {were|had been|have been} {prepared|ready} as a mixture of {up to|as much as} {three|3} isomers (rac5, meso5 and rac6) {from the|in the} reductive coupling of N-aryl iminoboronates with either cobaltocene or decamethylcobaltocene in acetonitrile. The interconversion of rac5 and rac6 isomers {via|by way of|through|by means of} rearrangement of their dynamic covalent B N bonds was investigated in {solution|answer|remedy|resolution|option} by redissolving isolated crystals. The aniline para substituent and catechol {within|inside} the amidoboronates tuned the distribution {between|in between|among|amongst|involving} the rac5 and rac6 isomers; the rac6 isomer predominated for amidoboronates {based on|according to|depending on|determined by} pyrocatechol with electron-withdrawing substituents and no interconversion was observed for the rac5 isomers of amidoboronates {based on|according to|depending on|determined by} tetrachlorocatechol. {Furthermore|Moreover|In addition|Additionally}, the rac5/rac6 distribution was altered by catechol exchange of pyrocatechol for tetrachlorocatechol exploiting the dynamic covalent B O bonds. Fmoc-D-Cys(Trt)-OH structure Price of Fmoc-Ser(tBu)-OH PMID:23812309
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