Abstract
trans-(2S.5S)-(1,1-Diphenylmethyl)pyrrolidine has been prepared from the corresponding diester in four steps and 54% overall yield. Key steps involve the nucleophilic addition of an organomagnesium reagent to a carbonyl compound promoted by cerium(III) chloride and the reductive removal of benzylic trimethylsilyloxyl groups with Me3SiCl-Nal-MeCN and water. (C) 2002 Elsevier Science Ltd. All rights reserved.
| Translated title of the contribution | 'Synthesis of new, highly hindered C-2-symmetric trans (2S,5S)-disubstituted pyrrolidines' |
|---|---|
| Original language | English |
| Article number | PII S0957-4166(02)00032-0 |
| Pages (from-to) | 87-93 |
| Number of pages | 7 |
| Journal | Tetrahedron: Asymmetry |
| Volume | 13 |
| Issue number | 1 |
| Publication status | Published - 13 Feb 2002 |
Research Groups and Themes
- Organic & Biological
- Inorganic & Materials
Keywords
- DIELS-ALDER REACTION
- ALPHA-AMINO-ACIDS
- ASYMMETRIC-SYNTHESIS
- TRANS-2,5-DISUBSTITUTED PYRROLIDINES
- CHIRAL AUXILIARIES
- D-MANNITOL
- 2,5-DISUBSTITUTED PYRROLIDINES
- ENANTIOSELECTIVE SYNTHESIS
- CLAISEN REARRANGEMENTS
- NUCLEOPHILIC-ADDITION
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