ISSN:
0009-2940
Keywords:
N-Boryl amino acid esters
;
N,N-Dimethyl amino acid boryl esters
;
N-Boryl amino acid boryl esters
;
1,3,2-Oxazaborolidin-5-on derivatives
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Contributions to the Chemistry of Boron, 2021). - Borylation of Amino Acids by an Amino-imino-boraneReactions of (tert-butylimino)(2,2,6,6-tetramethylpiperidino)-borane (3) with amino acid esters or N,N-dimethyl amino acids lead to the N-borylated products 5 and boryl esters 11, respectively. Amino acids and 3 yield the O,N-bis-boryl compounds 13 and/or 1,3,2-oxazaborolidin-5-ones 14, depending on the size of the organyl substituent R at the α-carbon atom of the amino acid. Increasing the bulk of this group favours the formation of 14 with elimination of tert-butylamine. The five-membered OBNCC ring of 14 is planar according to an X-ray structure analysis of 14e. (2,6-Diisopropylphenylimino)(2,2,6,6-tetramethylpiperidino)borane reacts with amino acids similar to 3, but tetramethylpiperidine is eliminated on ring formation to produce 20. N-Monoalkyl amino acids and 3 predominantly give oxazaborolidin-5-ones.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19901230503
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