Synthesis of an Influenza Neuraminidase Inhibitor Intermediate via a Highly Diastereoselective Coupling Reaction
Organic Letters2002Vol. 4(9), pp. 1427–1430
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David M. Barnes, Maureen A. McLaughlin, Tetsuro Oie, Michael Rasmussen, Kent D. Stewart, Steven J. Wittenberger
Abstract
[reaction: see text]. A highly diastereoselective coupling reaction between TBSOP (3) and trityl sulfenimine 4 was developed which provided influenza neuraminidase inhibitor intermediate 7 in 80% yield and >99% de after crystallization. The reaction was shown to be reversible with the high diastereoselectivity resulting from a favorable H-bonding interaction in the major diastereomer.
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