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5. Z/E Stereoselective synthesis of β-bromo Baylis–Hillman ketones using MgBr2 as promoter via a one-pot three-component reaction

Author

Wei, Han-Xun, Jasoni, Richard L., Hu, Jiali, Li, Guigen, and Paré, Paul W.

Subjects
*OXO compounds, *KETOACIDOSIS, *LIGHT metals, *MAGNESIUM group
Abstract

The first time steroselective synthesis of (Z)-β-bromo Baylis–Hillman ketones has been achieved using a one-pot three-component reaction. The new system uses MgBr2 as both the Lewis acidic promoter and the bromine source for the Michael-type addition with α,β-acetylenic ketones to form an active β-bromo allenolate intermediate, which in turn attacks various aldehydes to afford β-bromo Baylis–Hillman adducts in good yields and Z-selectivity. [Copyright &y& Elsevier]

Published
2004
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