Mild Oxidative Cleavage of 9‐BBN‐Protected Amino Acid Derivatives

European Journal of Organic Chemistry

Volumn 2015, Issue 17, 2015, Pages 3767-3770

  Ankner, Tobias ^a   Norberg, Thomas ^a   Kihlberg, Jan ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

Amino acids; Oxidation; Protecting groups

Indexed keywords

EID: 85027922839     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201500361     Document Type: Article

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37. Water, TFA, acetic acid, pyridine, BF3·OEt2, ammonium formate were added without observing any increase in deprotection rate.
38. SelectFluor® is known to be a potent oxidant and a source of electrophilic fluorine.
39. Over oxidation of reactive amino acids is a concern when using strong oxidizing agents such as TFPAA. Not surprisingly, 9‐BBN‐protected tryptophan yielded only a cyclized, oxidized product upon exposure to TFPAA. We assume that substrates containing sulfur, e.g. methionine, will also be oxidized.
40. TFPAA was generated immediately before use by adding TFAA (5 mmol, 695 μL) to a stirred suspension of urea‐hydrogen peroxide (5 mmol, 470 mg) in acetonitrile (8 mL). After 20 min the volume of the TFPAA solution was adjusted to 10 mL.