期刊
TETRAHEDRON
卷 64, 期 40, 页码 9423-9429出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.07.087
关键词
bis-thiourea; organocatalyst; Morita-Baylis-Hillman; enantioselective reaction
资金
- Mitubishi Chemical Corporation
- Uehara Memorial Foundation
- Nagase Science and Technology Foundation
- JSPS
Here, we describe our studies on the thiourea-catalyzed Morita-Baylis-Hillman (MBH) reaction. Chemoselective activation of carbonyl compounds via hydrogen bonding to thiourea as a catalyst is the key to drastic rate acceleration of this reaction. The application of chiral bis-thiourea-type organocatalysts, which can form a chiral double hydrogen-bonding network, is effective for enantioselective MBH reaction. A cooperative system of bis-thiourea compounds, synthesized from 1,2-diaminocyclohexane, and a Lewis base effectively promotes the MBH reaction at lower temperature, affording the MBH adducts in 33-95% yield with 44-90% ee. A plausible transition state model of the enantioselective MBH reaction is presented. (C) 2008 Elsevier Ltd. All rights reserved.
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