Allyl Cyanate-to-isocyanate Rearrangement for the Synthesis of Quaternary Stereocenter with Nitrogen Substituent
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- ICHIKAWA Yoshiyasu
- Laboratory of Natural Products, Faculty of Science, Kochi University
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- YAMAUCHI Eiji
- Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya University
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- ISOBE Minoru
- Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya University
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The stereochemistry and efficiency of an allyl cyanate-to-isocyanate rearrangement for the construction of quaternary stereocenter with nitrogen substituent was investigated by the synthesis of (R)-α-methylphenylalanine. The rearrangement was found to be stereospecific, and the chirality of allyl carbamate was transferred to that of the quaternary carbon bearing isocyanate group. These results establish that an allyl cyanate-to-isocyanate rearrangement is a useful method for the synthesis of natural products, that contain the quaternary carbon with nitrogen substituent.
収録刊行物
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- Bioscience, Biotechnology, and Biochemistry
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Bioscience, Biotechnology, and Biochemistry 69 (5), 939-943, 2005
公益社団法人 日本農芸化学会
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詳細情報 詳細情報について
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- CRID
- 1390282681451480960
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- NII論文ID
- 130000030324
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- NII書誌ID
- AA10824164
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- ISSN
- 13476947
- 09168451
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- NDL書誌ID
- 7322422
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- PubMed
- 15914913
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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