Stereodivergent Synthesis of Chiral 2-Alkenylaziridines: Palladium(0)-Catalyzed 2,3-cis-Selective Aziridination and Base-Mediated 2,3-trans-Selective Aziridination
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- Ohno Hiroaki
- Graduate School of Pharmaceutical Sciences, Osaka University
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- Takemoto Yoshiji
- Graduate School of Pharmaceutical Sciences, Kyoto University
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- Fujii Nobutaka
- Graduate School of Pharmaceutical Sciences, Kyoto University
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- Tanaka Tetsuaki
- Graduate School of Pharmaceutical Sciences, Osaka University
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- Ibuka Toshiro
- Graduate School of Pharmaceutical Sciences, Kyoto University
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Abstract
Whereas treatment of the allylic mesylates of N-protected 2-alkyl-4-amino-(E)-2-alken-1-ols with sodium hydride in DMF yields exclusively the corresponding thermodynamically less stable 2,3-trans-2-alkenyl-3-alkylaziridines, exposure of the methyl carbonates of N-protected 2-alkyl-4-amino-(E)-2-alken-1-ols to a catalytic amount of Pd(PPh3)4 in THF or 1,4-dioxane affords predominantly the corresponding thermodynamically more stable 2,3-cis-2-alkenyl-3-alkylaziridines. The kinetically favored trans-selective aziridination would be attributed to the allylic 1,3-strain in aza-anionic intermediates. The conformational analysis of the sterically highly congested 2-alkenylaziridines thus obtained is also presented.
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 52 (1), 111-119, 2004
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390282679147934336
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- NII Article ID
- 110003615486
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- NII Book ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 6795034
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- PubMed
- 14709877
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- Abstract License Flag
- Disallowed