Constrained amino acids. An approach to the synthesis of 3-substituted prolines
β Scribed by Philip P. Waid; Gary A. Flynn; Edward W. Huber; Jeffrey S. Sabol
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- French
- Weight
- 164 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
Preparation of 3-substituted prolines was achieved by extension to Solid Phase Organic Synthesis (SPOS) of the amino-zinc-enolate cyclization we have recently described. I Functionalizations of proline at C-3 were considered by nucleophilic substitutions of an iodo derivative obtained on the resin.
Enantiomerically pure ot-allyl-N-Boc-aminoamides were prepared by Curtius rearrangement of tx,ct-dialkyl chiral 2-cyanoesters obtained by the diastereoselective allylation of chiral 2-cyanoesters according to a modification of our previously described procedure.
The synthesis of a series of novel (t-amino acids based on the nucleophilic substitution of protected 2-amino-4-bromobutanoic acid (1) is described. Basic, acidic or neutral amino acids can be obtained; chimerical amino acids carrying a coenzyme type structure in the side chain, multifunctional amin