Diastereoselective Cyclization of 6-Octen-1-als with Rhodium(I)-Complex

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Abstract

In Rh(I) (Wilkinson)-catalyzed cyclization of 6-octen-1-als, the formation of cis-cyclohexanols is in contrast to Lewis acid-catalyzed cyclization, which affords predominantly the trans-cyclohexanols. However, 6-octen-1-als with a cyclic acetal (1,3-dioxane or 1,3-dioxolane) at the C_3-position were stereoselectively cyclized to only the trans-products.The aldehyde with a chiral protecting group ((4R, 6R)-dimethyl-1,3-dioxane with the C_2-axis) at the C_3-position was diastereoselectively cyclized to the trans-cyclohexanol, and on a basis of the absolute stereochemistry of the cyclized product, the cyclization mechanism is tentatively proposed. The effect of 4R-methyl-1,3-dioxane at the C_3-position was also examined.

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Details 詳細情報について

  • CRID
    1570009752554647936
  • NII Article ID
    110003627856
  • NII Book ID
    AA00602100
  • ISSN
    00092363
  • Text Lang
    en
  • Data Source
    • CiNii Articles

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