Iodine-mediated Ring Closing Alkene Iodoamination with N-Debenzylation for the Asymmetric Synthesis of Polyhydroxylated Pyrrolidines

Stephen G. Davies; Rebecca L. Nicholson; Paul D. Price; Paul M. Roberts; Andrew D. Smith

doi:10.1055/s-2004-820031

LETTER

Iodine-mediated Ring Closing Alkene Iodoamination with N-Debenzylation for the Asymmetric Synthesis of Polyhydroxylated Pyrrolidines

Stephen G. Davies*, Rebecca L. Nicholson, Paul D. Price, Paul. M. Roberts, Andrew D. Smith
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK
e-Mail: steve.davies@chemistry.oxford.ac.uk;

Abstract

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Abstract

An iodine-mediated ring closing alkene iodoamination with N-debenzylation protocol provides a direct route for the asymmetric synthesis of polyhydroxylated pyrrolidines from homochiral β-amino acid derivatives.

Key words

conjugate addition - iodoamination - debenzylation - cyclisation - pyrrolidine

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Referenzen

References

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The crystal structure of the hemi-hydrate of 12 was solved; crystal data for 12, C₁₄H₂₅NO₅·0.5 (H₂O), colourless plate, M = 296.36, monoclinic, space group C121, a = 23.8038 (15) Å, b = 5.9100 (5) Å, c = 12.0009 (9) Å, U = 1654.3 (2) Å³, Z = 4, µ = 0.091, crystal dimensions 0.05 × 0.1 × 0.5 mm. A total of 2081 unique reflections were measured for 5<θ<30 and 1705 reflections were used in the refinement. The final parameters were wR₂ = 0.053 and R₁ = 0.045 [I>3σ(I)]. Crystallographic data (excluding structure factors) has been deposited with the Cambridge Crystallographic Data Centre (CCDC 225944).