22985-61-1Relevant articles and documents
Application of an intramolecular Stetter reaction to access trans,syn,trans-fused pyrans
McErlean, Christopher S. P.,Willis, Anthony C.
, p. 233 - 236 (2009)
The use of a commercially available thiazolium salt facilitated an intramolecular Stetter reaction between an aliphatic aldehyde and an acrylate unit, which delivered a trans,syn-fused bicyclic pyranone in high yield as a single diastereomer. The pyranone
Carboxylates as Nucleophiles in the Enantioselective Ring-Opening of Formylcyclopropanes under Iminium Ion Catalysis
Díaz, Estibaliz,Reyes, Efraim,Uria, Uxue,Carrillo, Luisa,Tejero, Tomas,Merino, Pedro,Vicario, Jose L.
supporting information, p. 8764 - 8768 (2018/05/30)
In this work, carboxylic acids, which are typically regarded as poor nucleophiles, are demonstrated to be competent reagents to promote the ring-opening of formylcyclopropanes after activation of the latter through iminium ion formation. Under optimized r
Directing abilities of alcohol-derived functional groups in the hydroformylation of olefins
Ren, Li,Crudden, Cathleen M.
, p. 1746 - 1750 (2007/10/03)
The hydroformylation of allylic and homoallylic alcohols and their derivatives using cationic and neutral rhodium complexes has been examined. The highest diastereoselectivity (87:13) was observed in the reaction of 1-methoxymethoxy-2-methylenecyclohexane. Higher yields and similar selectivities were obtained in the reaction of the TBDMS-protected alcohol. The major diastereomer results from hydroformylation syn to the functional group, which would suggest a directing effect. However, hydroformylation of 3-methylene-1-cyclohexanol derivatives occurs on the face opposite to the directing group in the major isomer. These data, in addition to the results of hydroformylation of 1-methyl-2-methylenecyclohexane, suggest that inherent conformational preferences are of significant importance in determining the product distribution and that the directing power of simple alcohols and their derivatives is moderate at best under the conditions examined in this study.