Rhodium catalysed tandem hydrosilation cyclisation reaction

Work has begun on defining the scope of a novel tandem hydrosilylation cyclisation reaction as a general method for the synthesis of substituted carbocycles. Part I: Substituted cyclopentanols are accessible from 4-pentenals in moderate yield and cis selectivity. When R=CO2Me, a reversal in selectivity can be effected through the choice of the catalytic system. Part II: This methodology is compatible with 4, 5-substitution of the parent substrate, generating functionalised cyclopentanols in moderate selectivity and good yield. Part III; Tandem hydrosilylation cyclisation chemistry is applicable to the synthesis of substituted cyclohexanols. Conclusion: This novel chemistry provides a simple entry from lactols to highly substituted cyclopentanols and cyclohexanols in moderate yield and selectivity.