Publication: A new alkylation method for heptalene-4,5-dicarboxylates and of one of their pseudoester forms
A new alkylation method for heptalene-4,5-dicarboxylates and of one of their pseudoester forms
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Abou-Hadeed, K., Molnar, Z. A., Göksaltık, P., Kunz, R. W., Linden, A., & Hansen, H.-J. (2012). A new alkylation method for heptalene-4,5-dicarboxylates and of one of their pseudoester forms. Helvetica Chimica Acta, 95(6), 885–921. https://doi.org/10.1002/hlca.201100510
Abstract
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Dimethyl heptalene-4,5-dicarboxylates† undergo preferentially a Michael addition reaction at C(3) with α-lithiated alkyl phenyl sulfones at temperatures below −50°, leading to corresponding cis-configured 3,4-dihydroheptalene-4,5-dicarboxylates (cf. Table 1, Schemes 3 and 4). The corresponding heptalenofuran-1-one-type pseudoesters of dimethyl heptalene-4,5-dicarboxylates (Scheme 5) react with [(phenylsulfonyl)methyl]lithium almost exclusively at C(1) of the furanone group (Scheme 6). In contrast to this expected behavior, the uptake
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- Abou-Hadeed, Khaled
- Molnar, Zoltàn A
- Göksaltık, Pinar
- Kunz, Roland W
- Hansen, Hans-Jürgen
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Abou-Hadeed, K., Molnar, Z. A., Göksaltık, P., Kunz, R. W., Linden, A., & Hansen, H.-J. (2012). A new alkylation method for heptalene-4,5-dicarboxylates and of one of their pseudoester forms. Helvetica Chimica Acta, 95(6), 885–921. https://doi.org/10.1002/hlca.201100510
