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 language | English (US) |
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Pages (from-to) | 1314-1318 |
Number of pages | 5 |
Journal | Journal of Organic Chemistry |
Volume | 67 |
Issue number | 4 |
DOIs | |
State | Published - Feb 22 2002 |
Externally published | Yes |
ASJC Scopus subject areas
- Organic Chemistry