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Synfacts 2013; 9(1): 0081
DOI: 10.1055/s-0032-1317739
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed β-Arylation of α-Amino Esters

Contributor(s):
Paul Knochel
,
Andreas K. Steib
Aspin S, Goutierre A.-S, Larini P, Jazzar R, Baudoin O * Université Claude Bernard Lyon 1, France
Synthesis of Aromatic α-Aminoesters: Palladium-Catalyzed Long-Range Arylation of Primary Csp3 –H Bonds.

Angew. Chem. Int. Ed. 2012;
51: 10808-10811
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Further Information

Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

arylation - palladium - C–C coupling

Significance

A novel general β-arylation of protected alanine esters to yield synthetically useful (hetero)aryl alanine building blocks has been disclosed. The protocol utilizes a lithium amide to form an enolate that undergoes a palladium-catalyzed C–C coupling with various aromatic bromides.


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Comment

Interestingly, the reaction could be extended to α-amino acids bearing other linear alkyl chains. Arylation occurs preferentially at the terminal Csp3 –H bond, thus providing δ-, ε- and even ζ-arylated products. All products could be deprotected via hydrogenolysis to give the respective amines.


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