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Development of Asymmetic Deacylative Allylation
Grenning, Alexander J. Van Allen, Christie K. Maji, Tapan Lang, Simon Bouyea Tunge, Jon A.
Grenning, Alexander J.
Van Allen, Christie K.
Maji, Tapan
Lang, Simon Bouyea
Tunge, Jon A.
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Abstract
Herein we present the development of asymmetric deacylative allylation of ketone enolates. The reaction directly couples readily available ketone pronucleophiles with allylic alcohols using facile retro-Claisen cleavage to form reactive intermediates in situ. The simplicity and robustness of the reaction conditions is demonstrated by the preparation of > 6 grams of an allylated tetralone from commercially available materials. Furthermore, use of non-racemic PHOX ligands allows intermolecular formation of quaternary stereocenters directly from allylic alcohols.
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2013-07-19
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American Chemical Society
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Grenning, A. J., Van Allen, C. K., Maji, T., Lang, S. B., & Tunge, J. A. (2013). Development of Asymmetric Deacylative Allylation. The Journal of Organic Chemistry, 78(14), 10.1021/jo400793a. http://doi.org/10.1021/jo400793a