期刊
TETRAHEDRON
卷 66, 期 25, 页码 4423-4427出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.04.044
关键词
Bicyclo[3.2.1]octan-8-one; Tandem reaction; Organocatalysis; Enantioselective; Cyclohexane-1,2-dione; Nitroalkene
资金
- Welch Foundation [AX-1593]
- NIH-NIGMS [SC1GM082718]
Bicyclo[3.2.1]octan-8-ones have been prepared from a tandem Michael Henry reaction between cyclohexane-1,2-diones and nitroalkenes using a quinine-derived thiourea as the catalyst. Although four stereogenic centers were created during the reaction, only two diastereomers were obtained in good diastereoselectivity and high enantioselectivity (92-99% ee). When 3-methylcyclohexane-1,2-dione (R(1)=Me) was used as the substrate, only the regioisomeric product of the corresponding thermodynamic enolate was obtained. (C) 2010 Elsevier Ltd. All rights reserved.
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