Substituted furans are synthesized by phosphine-mediated reductive condensation of γ-acyloxy butynoates. The method represents a powerful and mechanistically novel protocol for the convergent three-component construction of the title compounds. -(JUNG, C.-K.; WANG, J.-C.; KRISCHE*, M. J.; J. Am. Chem. Soc. 126 (2004) 13, 4118-4119; Dep. Chem. Biochem., Univ. Tex., Austin, TX 78712, USA; Eng.) -S. Adam 31-107
Amino alcohols P 0130Asymmetric Induction in Hydrogen-Mediated Reductive Aldol Additions to α-Amino Aldehydes Catalyzed by Rhodium: Selective Formation of syn-Stereotriads Directed by Intramolecular Hydrogen-Bonding. -In the presence of the Rh catalyst, vinyl ketones undergo reductive addition to monoprotected α-amino aldehydes with high levels of syn-aldol selectivity accompanied by high levels of anti--Felkin-Anh control. Intramolecular hydrogen bonding plays a key role in both activating the α-amino aldehyde toward the reaction and directing the facial selectivity.
Ketones P 0200Hydrogen-Mediated Aldol Reductive Coupling of Vinyl Ketones Catalyzed by Rhodium: High syn-Selectivity Through the Effect of Tri-2-furylphosphine. -Hydrogenation of methyl or ethyl vinyl ketone in the presence of structurally diverse aldehydes under optimized conditions A) results in reductive coupling to afford aldol products with exceptionally high levels of syn-diastereoselection. -(JUNG, C.-K.; GARNER, S. A.; KRISCHE*, M. J.; Org. Lett. 8 (2006) 3, 519-522; Dep. Chem. Biochem., Univ. Tex., Austin, TX 78712, USA; Eng.) -R. Steudel 25-074
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