Synthesis of spiro-cyclopropane derivatives containing multiple chiral centers |
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Authors: | Hui Huang Qinghua Chen |
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Institution: | (1) Department of Chemistry, Beijing Normal University, 100875 Beijing, China;(2) Department of Chemistry, Tonghua Teacher’s College, 134002 Tonghua, China |
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Abstract: | Tandem asymmetric double Michael addition/internal nucleophilic substitution of the novel chiral source, 5-(l-menthyloxy)-3-bromo-2 (5H)-furanone with nucleophilic alcohol compounds has been investigated. The tandem asymmetric reaction
can afford four new stereogenic centers with one reaction and give optically pure spiro-cyclopropane derivatives 5a–5d which
are difficult to obtain by routine methods. The synthetic method for 5a–5d was studied in de-tail and the new compounds were
identified on the basis of their analytical data and spectroscopic data, such as α]20, IR,1H NMR,13C NMR, MS and elementary analysis. The absolute configuration of the sprio 5-l-menthyloxy-3-bromobutyrolactocyclopropane-3”, 3’ (4’-methyloxy-5’-menthyloxybutyrolactone) ] (5a) was established by X-ray
crystallography. The work can provide important synthetic strategy in synthesis of some new optically active spiro-cyclopropane
analogues and some biologically active molecules with complex structure.
Project supported by the National Natural Science Foundation of China (Grant No. 29672004). |
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Keywords: | 5-( l-menthyloxy)-3-bromo-2(5H)-furanone tandem reaction asymmetric double Michael addition /internal nucleophilic substitution crystal structure spiro-cyclopropane derivatives with multiple chiral centers |
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