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Synlett 1997; 1997(1): 22-24
DOI: 10.1055/s-1997-699
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Heterocyclisation via 1,3-Cyclic Sulfates, Asymmetric Synthesis of (+)-Sedridine

Benjamin J. Littler1 , Timothy Gallagher1 , Ian K. Boddy2 , Peter D. Riordan2
  • 1School of Chemistry, University of Bristol, Bristol BS8 1TS U.K.
  • 2AgrEvo UK Ltd., Chesterford Park, Saffron Walden CB10 1XL U.K.
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Publication Date:
22 March 2004 (online)

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1,3-Cyclic sulfates (1b-d) participate in heterocyclisation reactions to give pyrrolidines (2b) and piperidines (2c/d). Cyclic sulfate activation, when coupled to the enantio- and diastereoselective generation of 1,3-diols, provides a synthesis of (+)-sedridine (9).

1,3-cyclic sulfates - heterocyclisation - pyrrolidines - piperidines