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- W2024840129 abstract "Abstract The addition reaction of carbon nucleophiles to cis-substituted cyclopropanecarbaldehydes was systematically investigated. Ab initio calculations of model cyclopropanecarbaldehydes suggested that the bisected s-cis and s-trans conformers are the only two minimum energy conformers, which are stabilized due to the π-donating stereoelectronic effect of the cyclopropane ring. The experimental results of a series of substrates, that is, cyclopropanecarbaldehydes 1–5 bearing a cis-(tert-butyldiphenylsilyloxy)methyl group, a cis-benzyloxymethyl group, a cis-(p-methoxybenzyloxy)methyl group, cis-N,N-diethylcarbamoyl and trans-phenyl groups, and cis-(tert-butyldiphenylsilyloxy)methyl and trans-phenyl groups, respectively, showed that highly anti-selective Grignard additions could be realized. It turned out that it occurred via an unusual 7-membered 1,4-chelation-controlled pathway. Highly stereoselective Grignard addition via the chelation-controlled pathway occurred even in the reaction of the usually non-chelating silyl ether-type substrate 5 . The results have great importance because the 1,4-chelation-controlled stereoselective addition reactions can indeed be realized. Under non-chelation conditions, the syn-products were produced with moderate stereoselectivity, which are likely to be formed via the bisected s-cis conformation-like transition state stabilized by the characteristic orbital interaction. These reactions, especially the chelation-controlled reaction, should be useful because of their t stereoselectivity and stereochemical predictability." @default.
- W2024840129 created "2016-06-24" @default.
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- W2024840129 date "2004-11-23" @default.
- W2024840129 modified "2023-09-24" @default.
- W2024840129 title "The Unusual 1,4-Chelation-Controlled Nucleophilic Addition to Aldehydes with High Stereoselectivity. A Systematic Study of Stereoselectivity in the Addition Reaction of Carbon Nucleophiles to cis-Substituted Cyclopropanecarbaldehydes." @default.
- W2024840129 cites W2949141658 @default.
- W2024840129 doi "https://doi.org/10.1002/chin.200447063" @default.
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