Highly diastereoselective sequential Michael-aldol reactions of methyl 2-chloro-2-cyclopropylideneacetate with Grignard reagents and aldehydes
2006 | journal article. A publication with affiliation to the University of Göttingen.
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Highly diastereoselective sequential Michael-aldol reactions of methyl 2-chloro-2-cyclopropylideneacetate with Grignard reagents and aldehydes
Dalai, S.; Limbach, M.; Zhao, L.; Tamm, M.; Sevvana, M.; Sokolov, V. V. & de Meijere, A. (2006)
Synthesis,(3) pp. 471-479. DOI: https://doi.org/10.1055/s-2006-926276
Documents & Media
Details
- Authors
- Dalai, S.; Limbach, M.; Zhao, L.; Tamm, M.; Sevvana, Madhumati; Sokolov, Viktor V.; de Meijere, Armin
- Abstract
- Grignard reagents, especially isopropylmagnesiurn chloride, smoothly undergo Michael addition onto methyl 2-bromo- and 2-chloro-2-cyclopropylideneacetate (1-Cl), and the thus formed magnesium enolates are particularly efficiently trapped with aromatic aldehydes. This one-pot reaction provides highly substituted chlorohydrines, mostly in high yields (10 out of 18 examples with 72-92%) and as pure (2S ,3R )-diastereomers (anti-aldols). These chlorohydrines can be transformed to Darzens-type alpha,beta-epoxyesters in good yields, as demonstrated for one example.
- Issue Date
- 2006
- Status
- published
- Publisher
- Georg Thieme Verlag Kg
- Journal
- Synthesis
- ISSN
- 0039-7881
