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Synlett 2004(5): 0901-0903  
DOI: 10.1055/s-2004-820031
LETTER
© Georg Thieme Verlag Stuttgart · New York

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;
Further Information

Publication History

Received 4 February 2004
Publication Date:
04 March 2004 (online)

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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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18

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).