Abstract
Conjugate addition of N-benzyl-N-(R)-1-phenylethyl)amme (R)-5 to (R)-(E)-tert-butyl 5-((tert-butyldimethylsilyl)oxy)-4-methyl-2-pentenoate (10a) produced the (3S,4R)-syn-adduct 14 with essentially 100% de in 84% yield, whereas the addition of (S)-5 to 10a afforded the (3R,4R)-anti-adduct 15 with essentially 100% de in 95% yield. The syn adduct 14 was converted upon sequential treatment with lithium diisopropylamide-methylaluminum dichloride-acetaldehyde to the key intermediate 21; the diastereoisomer ratio of 21 to other diasteroisomers was 80:20. Conversion of 21 to a 1β-methylcarbapenem key intermediate 26 was carried out readily according to the known procedures.
Original language | English |
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Pages (from-to) | 143-148 |
Number of pages | 6 |
Journal | Journal of Organic Chemistry |
Volume | 60 |
Issue number | 1 |
DOIs | |
Publication status | Published - 1995 Jan 1 |
ASJC Scopus subject areas
- Organic Chemistry