Stereoselective Epoxide Generation with Cyclic Rhodium Carbenoids: A New Access to Spiro-indolooxiranes

Abstract

The reaction of cyclic diazoamides with aryl aldehydes catalyzed by rhodium(II) acetate leads to intermolecular stereoselective epoxide ring formation. A series of spiro-indolooxiranes has been synthesized following the described method in a facile manner. The use of aryl dialdehydes in the course of reaction of cyclic diazoamide resulted the formation of bis-spiro-indolooxiranes

Key words

carbenoids - diazo ketones - oxiranes - rhodium(II) acetate - spiro compounds

References

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16

Crystal data for compound 3g: Colorless rectangular crystal. C₂₃H₁₉NO₃, M = 357.39, 0.50 × 0.08 × 0.05 mm³, triclinic, space group p-1 with a = 5.9327(13) Å, b = 10.800(2) Å, c = 14.812(3) Å, α = 90.925(4)°, β = 94.846(4)°, γ = 101.966(4)°, V = 924.6(4) ų, T = 293(2) K, R ₁ = 0.0496, wR ₂ = 0.1204 on observed data, z = 2, D _calcd = 1.284 g cm^-3, F(000) = 376, Absorption coefficient = 0.085 mm^-1, λ = 0.71073 Å, 3567 reflections were collected on a smart apex ccd single crystal CCD diffractometer, 2632 observed reflections [I≥2σ (I)]. The largest difference peak and hole = 0.234 and -0.246e Å^-3, respectively. The structure was solved by direct methods and refined by full-matrix least squares on F ² using SHELXL-97 software.

17

Crystallographic data for 3g have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no CCDC-222010. Copies of the data can be obtained free of charge on application to 12, Union Road, Cambridge CB2 1EZ, UK. [fax: [phone]; e-mail: [e-mail]].