Synthesis of (2S)-4,4-difluoroproline, (2S,4R)-4-fluoroproline and their derivatives from (S)-aspartic acid [1]
✍ Scribed by Klaus Burger; Martin Rudolph; Susanna Fehn; Norbert Sewald
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- English
- Weight
- 435 KB
- Volume
- 66
- Category
- Article
- ISSN
- 0022-1139
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📜 SIMILAR VOLUMES
The tide compounds were prepared from key intermediates readily obtained by the stereoselective Diels-Alder reaction of (Z)-2-pbenyl-4-[(S)-2,2-dimethyl-l,3dioxolan-4-ylmethylene]-5(4H)-oxazolone, a chiral az-lactone derived from (R)glyceraldehyde and cyclopentadiene.
## Abstract A new synthetic route to enantiopure (2__S__,4__R__)‐4‐hydroxypipecolic acid from commercial ethyl (3__S__)‐4‐chloro‐3‐hydroxybutanoate is reported. The synthesis is based on the Pd‐catalyzed methoxycarbonylation of a 4‐alkoxy‐substituted δ‐valerolactam‐derived vinyl triflate followed b