Synfacts 2008(2): 0177-0177  
DOI: 10.1055/s-2007-992489
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of α-Aryl Amino Acids via Sommelet-Hauser Rearrangement

Contributor(s): Mark Lautens, Frédéric Ménard
E. Tayama*, H. Kimura
Niigata University, Japan
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23. Januar 2008 (online)


The methodology expands the synthetic utility of the Sommelet-Hauser (SH) rearrangement. It is noteworthy for its operational simplicity as well as for its unprecedented selectivity for the [2,3]- vs [1,2]-rearrangement. Now, sterically hindered α-aryl amino acids can be prepared efficiently with high stereoselectivity. Importantly, the authors reported that both Stevens- and SH-rearranged products 4 and 6 can be accessed by a simple change in base and solvent.