Abstract
Asymmetric reactions of dodecanethiol with β-substituted phenyl vinyl ketones were studied using polymeric and monomeric cinchona alkaloids as chiral catalysts. The mode of stereoregulation (C(8), C(9)-control, C(3)-control) varied depending not only on the substituents at C(3) and C(6′) of the alkaloid molecule but also on the β-substituent of the unsaturated systems. The C(3)-control was observed when the steric environments of the enantioface differentiating step were sufficiently crowded (combination of polymer catalyst and bulky β-substituent).
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Kobayashi, N., Iwai, K. Functional Polymers. VII. On the C(3)-Control of Stereochemistry in Asymmetric Reactions Catalyzed by Polymeric Cinchona Alkaloids. Polym J 13, 263–271 (1981). https://doi.org/10.1295/polymj.13.263
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DOI: https://doi.org/10.1295/polymj.13.263