Journal
ORGANIC LETTERS
Volume 13, Issue 2, Pages 216-219Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol102613z
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Funding
- DFG [FOR 806]
- Fonds der chemischen Industrie
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A practical four-step synthesis of 3-alkyl-, vinyl-, and aryl-substituted proline derivatives, which are important building blocks for conformationally restrained peptide analogs, was developed. The method relies on a Cu-catalyzed 1,4-addition of Grignard reagents to N-protected 2,3-dehydroproline esters, efficiently prepared in a new one-pot protocol. The 1,4-addition products are obtained with good trans-selectivity (dr 5:1 to 25:1). A nonracemic sample of N-Cbz-3-vinylproline (74% ee) was obtained using Evans oxazolidinone as a chiral auxiliary.
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