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Highly Enantioselective Access to α-Dibenzylamino Ketones from Chiral Nonracemic α-Bromo α′-Sulfinyl Ketones by Dynamic Kinetic Resolution: Synthesis of (2R,1′S)-2-[1-(Dibenzylamino)alkyl]oxiranes

✍ Scribed by Pierre-Yves Géant; Jean Martínez; Xavier J. Salom-Roig

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 491 KB
Volume: 2011
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.201001403

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✦ Synopsis

A novel and efficient synthesis of enantiomerically pure αdibenzylamino αЈ-sulfinyl ketones starting from a mixture of both epimers of α-bromo αЈ-(R)-sulfinyl ketone has been realized through combined in situ substitution-epimerization in a so-called Dynamic Kinetic Resolution (DKR). The scope of the reaction has been examined, and four differently substi- [a]