Abstract
Five prolinol-based chiral auxilaries have been compared for the stereoselective synthesis of γ-butyrolactones via the sequence of N-acylation, Cα-allylation, and iodolactonization under both solution-phase and solid-phase conditions. Comparisons of stereoselectivity of both the Cα-allylation and iodolactonization processes indicate that incorporation of a non-C2-symmetric auxiliary as a polymer cross-link gives results superior to those obtained either in solution or with other non-C2-symmetric auxiliaries and comparable to those observed using a polymer-supported pseudo-C2-symmetric auxiliary.
Original language | English (US) |
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Pages (from-to) | 7769-7773 |
Number of pages | 5 |
Journal | Journal of Organic Chemistry |
Volume | 67 |
Issue number | 22 |
DOIs | |
State | Published - Nov 1 2002 |
ASJC Scopus subject areas
- Organic Chemistry