Hydroxylated Pyrrolidines. Enantiospecific Synthesis of all-cis 2,3,4,5-Substituted Pyrrolidine Derivatives from Serine

  1. Verma, S.K. 1
  2. Atanes, M.N. 1
  3. Busto, J.H. 1
  4. Thai, D.L. 1
  5. Rapoport, H. 1
  1. 1 University of California, Berkeley
    info

    University of California, Berkeley

    Berkeley, Estados Unidos

    ROR https://ror.org/01an7q238

Revue:
Journal of Organic Chemistry

ISSN: 0022-3263

Année de publication: 2002

Volumen: 67

Número: 4

Pages: 1314-1318

Type: Article

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DOI: 10.1021/JO011008+ PMID: 11846680 SCOPUS: 2-s2.0-0037154803 GOOGLE SCHOLAR

D'autres publications dans: Journal of Organic Chemistry

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Résumé

We report the enantiospecific synthesis of the sterically congested all-cis 2,3,4,5-substituted pyrrolidines 4, 5, and 6, from either D- or L-serine. Hemiaminal intermediate 13 is converted to the fully substituted pyrrolidine 15 by way of a tandem Wittig-Michael reaction. The endo stereochemistry of the C-3 methyl group of compound 15 is set by stereoselective reduction of the double bond in 11, driven by a preference for hydrogenation from the rear side of the molecule. The all-cis configuration of these fully substituted pyrrolidines has been established by X-ray analysis of compound 6. Removal of the benzenesulfonyl group from the highly substituted and functionalized intermediate 15 is successfully accomplished by sodium naphthalenide reduction.