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Synthesis 2010(15): 2515-2520  
DOI: 10.1055/s-0029-1218830
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Heck Reaction of Amino Acid Derived Vinyl Substrates in the Synthesis of Homotyrosinol Derivatives

Huan Liang, Yuan Zhou, Marco A. Ciufolini*
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada
Fax: +1(604)8228710; e-Mail: ciufi@chem.ubc.ca;
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Publication History

Received 2 February 2010
Publication Date:
17 June 2010 (online)

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Abstract

An avenue to homotyrosinol derivatives through a Heck coupling of 4-iodophenyl acetate with a vinylglycinol derivative required extensive screening of catalysts and conditions. The use of Pd(OAc)2 and N-phenylurea as the ligand ultimately provided excellent results.

Key words

coupling - Heck reaction - homotyrosine - palladium - N-phenylurea

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Ca. $100/gram as quoted in SciFinder.

11

There was no reaction in THF at temperatures below 60 ˚C. At reflux, the substrate was converted into complex mixtures of products.