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Synfacts 2008(2): 0168-0168  
DOI: 10.1055/s-2007-992491
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Practical Synthesis of Ambiphilic Silyl Intermediates

Contributor(s): Mark Lautens, Frédéric Ménard
S. Sen, M. Purushotham, Y. Qi, S. McN. Sieburth*
Temple University, Philadelphia, USA
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

The major interest of the authors was to develop a practical access to 5, which is a key intermediate in the synthesis of silanediol-based protease inhibitors. Not only did they succeed in this objective, but more importantly, they also described the ambiphilic reactivity of this intermediate. It was shown to behave as both an electrophile and a nucleophile and lead to a variety of adducts (6-10).