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Aluminum Iodide Promoted Highly Z-Stereoselective Synthesis of β-Iodo Morita-Baylis-Hillman Esters with Ketones as Aldol Acceptors

Sung Il Lee, Geum-Sook Hwang, Do Hyun Ryu*

*Department of Chemistry, Sungkyunkwan University, Suwon 440-746, Korea, Email:

S. Il Lee, G.-S. Hwang, D. H. Ryu, Synlett, 2007, 59-62.

DOI: 10.1055/s-2006-958421


Various ketones as the electrophiles react in a one pot three-component coupling with an aluminum allenoate intermediate derived from ethyl propiolate and alluminium iodide to yield β-iodo Morita-Baylis-Hillman adducts with high yield and excellent Z-stereoselectivity.

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proposed mechanism

Key Words

Baylis-Hillman Adducts, Vinyliodides, Multicomponent Reactions

ID: J60-Y2007-0040