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

フォーマット:

論文

責任表示:

Wei, Weilin ; Kobayashi, Masato ; Ukaji, Yutaka ; Inomata, Katsuhiko

言語:

英語

出版情報:

Elsevier BV / Japan Institute of Heterocyclic Chemistry, 2009-03-01

著者名:

• Wei, Weilin
• Kobayashi, Masato
• Ukaji, Yutaka
• Inomata, Katsuhiko

掲載情報:

Heterocycles

ISSN:

0385-5414      

巻:

78

通号:

3

開始ページ:

717

終了ページ:

724

バージョン:

author

概要:

金沢大学理工研究域物質化学系<br />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 ad … dition 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. 続きを見る

URL:

http://hdl.handle.net/2297/17577