Hydroxylated pyrrolidines. Enantiospecific synthesis of all-cis 2,3,4,5-substituted pyrrolidine derivatives from serine

Sharad K. Verma, M. Nieves Atanes, J. Hector Busto, Dung L. Thai, Henry Rapoport

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish (US)
Pages (from-to)1314-1318
Number of pages5
JournalJournal of Organic Chemistry
Volume67
Issue number4
DOIs
StatePublished - Feb 22 2002
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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