Abstract
An efficient one-pot, three-component coupling reaction for the synthesis of β-iodo-α-(hydroxyalkyl) acrylates has been developed. As the iodine source as well as the Lewis acid mediator, diethyl aluminium iodide undergoes a Michael-type addition with methyl propynoate to form an active β-iodo allenolate intermediate, which in turn attacks various aldehydes or ketones to afford β-iodo Baylis-Hillman adducts in excellent yields with high Z-selectivity.
Original language | English |
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Pages (from-to) | 5677-5680 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 43 |
Issue number | 32 |
DOIs | |
State | Published - Aug 5 2002 |
Keywords
- Baylis-Hillman adducts
- Diethyl aluminium iodide
- Methyl propynoate
- β-iodo-α-(hydroxyalkyl)acrylates