期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 131, 期 44, 页码 16018-+出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja907233q
关键词
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资金
- NSF [CHE-0848847]
- NIH
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [848847] Funding Source: National Science Foundation
A highly stereosetective synthesis of novel cyclically constrained gamma-amino acid residues is presented. The key step involves organocatalytic Michael addition of an aldehyde to 1-nitrocyclohexene. After aldehyde reduction, this approach provides optically active beta-substituted delta-nitro alcohols (96-99% ee), which can be converted to gamma-amino acid residues with a variety of substituents at the a position. We have used these new building blocks to prepare alpha/gamma-peptide foldamers that adopt a specific helical conformation in solution and in the solid state.
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