- Synthesis, X-ray crystallography, and reactions of N-acyl and N-carbamoyl succinimides
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A collection of N-acyl and N-carbamoyl succinimides were prepared by acylation of succinimide with acyl chlorides or by ethylene dichloride (EDC) coupling of carboxylic acids. The x-ray crystal structures of N-benzoyl and N-p-nitrobenzoyl succinimides were determined. The N-acyl succinimides were effective in acylating primary amines, a secondary amine, and an aromatic amine. Copyright
- Goodman, Cassie A.,Eagles, Joel B.,Rudahindwa, Leandre,Hamaker, Christopher G.,Hitchcock, Shawn R.
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supporting information
p. 2155 - 2164
(2013/07/25)
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- A practical synthesis of trans -3-substituted proline derivatives through 1,4-addition
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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.
- Huy, Peter,Neudoerfl, Joerg-Martin,Schmalz, Hans-Guenther
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supporting information; experimental part
p. 216 - 219
(2011/03/20)
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