Asymmetric reaction of chiral azomethines with organometallic reagents.

• 鈴木 雄二

• 高橋 浩

抄録

Reaction of (E)-(S)-N-(1-isopropyl-2-methoxyethyl)benzylideneamine (2) with ethylmagnesium bromide gave a mixture of (1S, 1'S)- and (1R, 1'S)-N-(1'-isopropyl-2'-methoxyethyl)-1-phenylpropylamines (3) (91 : 9%). (E)-(S)-N-(1-Isopropyl-2-methoxyethyl)propylideneamine (5) was treated with phenyllithium to give (1R, 1'S)- and (1S, 1'S)-3 (95 : 5%). On the other hand, reaction of (E)-(S)-N-(2-hydroxy-1-isopropylethyl)benzylideneamine (6) with ethylmagnesium bromide yielded a mixture of (1S, 1'S)- and (1R, 1'S)-N-(2'-hydroxy-1'-isopropylethyl)-1-phenylpropylamines (7) (78 : 22%). The absolute configurations of these amines were determined by circular dichroism (CD) spectroscopy and comparison with authentic samples synthesized by alternative methods.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 31 (8), 2895-2898, 1983

  公益社団法人 日本薬学会

キーワード

• phenylpropylamine

詳細情報

• CRID: 1390282679141963648
• NII論文ID: 130003769429
• DOI: 10.1248/cpb.31.2895
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/31/8/31_8_2895/_pdf
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可