書誌事項
- タイトル別名
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- A New Approach to Optically Active 1,2-Diaryl-1,2-diaminoethanes and 1,2-Diaryl-2-aminoethanols.
- コウガク カッセイ 1 2 ジアリール 1 2 ジアミノ エタン オヨビ 1
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説明
Widespread use of homochiral 1, 2-diary1-1, 2-diaminoethanes and 2-amino-1, 2-diarylethanols as chiral auxiliaries coupled with difficulties associated with their preparation prompted us to investigate new methodologies for their syntheses. For the preparation of this highly useful class of compounds, enantioselective imino pinacol coupling of p-anisylbenzal-imine was investigated using Zn-Cu couple in the presence of (+) -camphorsulfonic acid as a chiral auxiliary to give (R, R) -1, 2-diphenylethylenediamine derivative in high enantiomeric purity. Highly enantioselective reduction of 1, 2-bis (p-methoxyphenylimino) -1, 2-diphenylethane was also conducted with 0.5 mol% of the new oxazaborolidine, derived from L-threonine and a stoichiometric amount of BH3· THF, to give 1, 2-diphenylethylenediamine derivative in excellent enantiomeric purity. The subsequent deprotection of nitrogen atoms afforded (R, R) -1, 2-diphenylethylenediamine in enantiomerically pure form. Moreover, the reduction of 1, 2-diaryl-2-benzyloxyiminoethanones conducted using the above oxazaborolidine and BH3 ·SMe2 gave β-imino alcohols chemoselectively in high enantiomeric purity. Subsequent selective reduction of the imino functionality affords either syn- or anti-2-amino-1, 2-diarylethanols in high enantiomeric purity by choosing appropriate reduction conditions.
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 56 (8), 672-680, 1998
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
- 1390282680254896256
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- NII論文ID
- 10009343006
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- NII書誌ID
- AN0024521X
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- COI
- 1:CAS:528:DyaK1cXlt1Sit7o%3D
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 4548006
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- NDL
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- 抄録ライセンスフラグ
- 使用不可