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| LETTER | Synlett 2007: 0059-0062
DOI: 10.1055/s-2006-958421 |
© Georg Thieme Verlag Stuttgart · New York
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Aluminum Iodide Promoted Highly Z-Stereoselective Synthesis of β-Iodo Morita-Baylis-Hillman Esters with Ketones as Aldol Acceptors
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| Sung Il Leea, Geum-Sook Hwang*b, Do Hyun Ryu*a |
a Department of Chemistry, Sungkyunkwan University, Suwon 440-746, Korea
Fax: +82(31)2905976; e-Mail: dhryu@skku.edu;
b Korea Basic Science Institute, 5 St, Anam-Dong, Seongbuk-Gu, Seoul 136-701, Korea
Fax: +82(2)9200779; e-Mail: gshwang@kbsi.re.kr;
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Received
11 October 2006 |
Abstract
Aluminum iodide has been found to promote the efficient and highly stereoselective synthesis of (Z)-β-iodo-α-(hydroxyalkyl)acrylates via one-pot three-component coupling reactions. This new system has made it possible to utilize various ketones as the electrophiles, in order to react with an aluminum allenoate intermediate for the synthesis of β-iodo Morita-Baylis-Hillman adducts with high yield and excellent Z-stereoselectivity (>99%). Key words
Morita-Baylis-Hillman adduct - aluminum iodide - ketones - stereoselectivity - aldol reactions
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