1.
Chemistry
; 24(57): 15215-15218, 2018 Oct 12.
Article
in English
| MEDLINE
| ID: mdl-30102444
ABSTRACT
This report discloses the first example of catalytic arylhydroxylation of dehydroalanine with aryldiazonium salts. Aryldiazonium salts, which are generated from aniline precursors under partially aqueous conditions in continuous flow, efficiently reacted with dehydroalanine in the presence of 10-15â mol % ferrocene to furnish α-hydroxyarylalanine derivatives (up to 82 % yield). The reactions proceeded with regioselectivity, broad functional group tolerance, and without polymerization of the dehydroalanine. Furthermore, the products were used to access α-unnatural amino acids, important targets with application in drug development.