One pot synthesis of optically active 4-isoxazolines by asymmetric addition of alkynylzinc reagents to nitrones followed by cyclization

• Wei Weilin

• Kobayashi Masato

• Ukaji Yutaka

• Inomata Katsuhiko

• 小林 正和

• 宇梶 裕

• 猪股 勝彦

抄録

金沢大学理工研究域物質化学系

One pot synthesis of optically active 4-isoxazolines was achieved by asymmetric addition of alkynylzinc reagents to nitrones utilizing di(t-butyl) (R,R)-tartrate as a chiral auxiliary followed by cyclization. By addition of dimethylzinc, the cyclization step was accelerated to afford the corresponding 4-isoxazolines with up to 93% ee. Furthermore, a cyclized zinc intermediate could be trapped with formaldehyde to give the corresponding 2,3,4,5-tetrasubstituted 4-isoxazoline with 85% ee. © 2009 The Japan Institute of Heterocyclic Chemistry All rights reserved.

収録刊行物

• Heterocycles

  Heterocycles 78 (3), 717-724, 2009-03-01

  Elsevier BV / Japan Institute of Heterocyclic Chemistry

キーワード

• Alkynylzinc Reagent
• Asymmetric Addition to Nitrone
• Cyclization
• One Pot Synthesis
• Optically Active 4-Isoxazoline

詳細情報

• CRID: 1390012943806035456
• NII論文ID: 120001342276
• NII書誌ID: AA00663739
• ISSN: 03855414
• DOI: 10.24517/00010940
• NDL書誌ID: 10157170
• Web Site: http://hdl.handle.net/2297/17577
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I10157170
• 本文言語コード: en
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