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Synthesis of (R)- and (S)-3-(tert-butyldimethylsilyloxy)-1-pyrroline N-oxides — chiral nitrones for synthesis of biologically active pyrrolidine derivative, Geissman-Waiss lactone

✍ Scribed by Shun-Ichi Murahashi; Hiroaki Ohtake; Yasushi Imada

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
147 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

Tungstate-catalyzed oxidation of O-tert-butyldimethylsilyl (O-TBDMS) protected (R)-3-hydroxypyrrolidine ((R)-

2), derived from trans-4-hydroxy-L-proline, gave O-TBDMS protected (R)-3-hydroxy-l-pyrroline N-oxide ((R)-1), which is a new chiral precursor for the synthesis of Geissman-Waiss lactone. The enantiomeric nitrone (S)-I was also prepared by the oxidation of (S)-2 derived from L-malic acid.

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis of (R)- a
ChemInform Abstract: Synthesis of (R)- and (S)-3-(tert-Butyldimethylsilyloxy)-1-pyrroline N-Oxides — Chiral Nitrones for Synthesis of Biologically Active Pyrrolidine Derivative, Geissman—Waiss Lactone.
✍ S.-I. MURAHASHI; H. OHTAKE; Y. IMADA 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 36 KB 👁 1 views

Synthesis of (R)-and (S)-3-(tert-Butyldimethylsilyloxy)-1-pyrroline N-Oxides -Chiral Nitrones for Synthesis of Biologically Active Pyrrolidine Derivative, Geissman-Waiss Lactone. -Tungstatemediated oxidation of the chiral Tbs-protected 3-hydroxypyrrolidines (II) provides the required nitrones (III)