Heterocycle Synthesis via Radical Addition-Cyclization of Oxime Ethers.
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- Miyabe Hideto
- Kobe Pharmaceutical University
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- Miyata Okiko
- Kobe Pharmaceutical University
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- Naito Takeaki
- Kobe Pharmaceutical University
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Oxime ethers connected by a tether to aldehydes or ketones efficiently cyclized via stannyl radical addition-cyclization to give a new entry to heterocyclic amino alcohols. The SmI2-induced radical cyclization was found to be effective for preparing cyclic trans-amino alcohols. These radical reactions provide a novel method for the synthesis of (-) -balanol, aminocyclitols, 1-deoxynojirimycin, 2-substituted 5-amino-4-piperidinol, and nucleoside analogs. The sulfanyl radical addition-cyclization-elimination reaction was developed, which was successfully applied to the synthesis of (-) -kainic acid. The sulfanyl radical addition-cyclization of oxime ethers gave a method for synthesis of rigidified cyclic β-amino acids. The carbon radical addition-cyclization reaction of substrates having two different radical acceptors such as acrylate and aldoxime ether moieties proceeded even in aqueous media via a diastereoselective tandem C-C bond-forming process, providing a method for asymmetric synthesis of γ-butyrolactones and γ-amino acids.
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 60 (11), 1087-1094, 2002
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390001205277868544
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- NII論文ID
- 10012595076
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- NII書誌ID
- AN0024521X
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- COI
- 1:CAS:528:DC%2BD38XoslOitbc%3D
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- ISSN
- 18836526
- 00379980
- http://id.crossref.org/issn/00379980
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- NDL書誌ID
- 6351150
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可