Selected Paper : Synthesis of β-Hydroxy-α,α-disubstituted Amino Acids through the Orthoamide-Type Overman Rearrangement of an α,β-Unsaturated Ester and Stereodivergent Intramolecular S[N]2' Reaction : Development and Application to the Total Synthesis of Sphingofungin F
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<jats:title>Abstract</jats:title> <jats:p>The development of a two-step synthesis for β-hydroxy-α,α-disubstituted amino acid derivatives from cyclic orthoamide is reported. The first step is the orthoamide-type Overman rearrangement of an α,β-unsaturated ester to give a sterically hindered α,α-disubstituted amidoester. The α,β-unsaturated ester is known to be a challenging substrate in the conventional Overman rearrangement due to the competitive aza-Michael reaction. However, suppression of the aza-Michael reaction is realized by two factors; 1) the high reaction temperature, and 2) an alkyl substituent at the α-position. The second step is stereodivergent intramolecular SN2′ reaction for the installation of a hydroxy group at the β-position. Either syn- or anti-type SN2′ reaction is possible by simply changing the reaction conditions. The developed method can provide all four possible stereoisomers of the β-hydroxy-α,α-disubstituted amino acid, and is successfully applied to the total synthesis of sphingofungin F.</jats:p>
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 91 (4), 594-607, 2018-04
Tokyo : Chemical Society of Japan
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詳細情報 詳細情報について
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- CRID
- 1520291856053242880
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- NII論文ID
- 130006707638
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- NII書誌ID
- AA00580132
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- ISSN
- 00092673
- 13480634
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- NDL書誌ID
- 028935289
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- 本文言語コード
- en
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- NDL 雑誌分類
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- ZP1(科学技術--化学・化学工業)
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- データソース種別
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- NDL
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