期刊
ORGANIC LETTERS
卷 15, 期 18, 页码 4770-4773出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol402129h
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资金
- W. W. Caruth, Jr. Endowed Scholarship
- Robert A. Welch Foundation [1-1748]
- National Science Foundation [NSF CAREER 1150875]
- Sloan Research Fellowship
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1150875] Funding Source: National Science Foundation
Unnatural cyclic amino acids are valuable tools in biomedical research and drug discovery. A two-step stereoselective strategy for converting simple glycine-derived aminoesters into unnatural cyclic amino acid derivatives has been developed. The process includes a palladium-catalyzed tandem allylic amination/[2,3]-Stevens rearrangement followed by a ruthenium-catalyzed ring-closing metathesis. The [2,3)-rearrangement proceeds with high diastereoselectivity through an exo transition state. Oppolzer's chiral auxiliary was utilized to access an enantiopure cyclic amino acid by this approach, which will enable future biological applications.
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