Stereoselective Synthesis of β-Hydroxyphenylalanines Using Imino 1,2-Wittig Rearrangement of Hydroximates
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- Miyata Okiko
- Kobe Pharmaceutical University
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- Asai Hiroshi
- Kobe Pharmaceutical University
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- Naito Takeaki
- Kobe Pharmaceutical University
書誌事項
- タイトル別名
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- Stereoselective Synthesis of .BETA.-Hydroxyphenylalanines Using Imino 1,2-Wittig Rearrangement of Hydroximates
- Stereoselective Synthesis of ベータ Hydroxyphenylalanines Using Imino 1 2 Wittig Rearrangement of Hydroximates
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説明
The imino 1,2-Wittig rearrangement of hydroximates containing a furan ring provides a novel method for the synthesis of β-hydroxy-α-amino acids. Upon treatment with LDA, hydroximates smoothly underwent the rearrangement to give Z-2-hydroxyoxime ethers in good yield, which were converted into both cis- and trans-oxazolidinones with high stereoselectivity. The cis- and trans-oxazolidinones were stereoselectively converted into erythro- and threo-β-hydroxyphenylalanines, respectively, via the oxidative cleavage of a furan ring, ring-opening of oxazolidinone, and deprotection.
収録刊行物
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- ＣＨＥＭＩＣＡＬ ＆ ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ ＢＵＬＬＥＴＩＮ
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ＣＨＥＭＩＣＡＬ ＆ ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ ＢＵＬＬＥＴＩＮ 53 (4), 355-360, 2005
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390282679146424192
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- NII論文ID
- 10016652841
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- NII書誌ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL書誌ID
- 7292000
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- PubMed
- 15802831
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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
- PubMed
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可
