Catalytic asymmetric dialkynylation reaction of α-dinitrone by utilizing tartaric acid ester as a chiral auxiliary

• Serizawa Masakazu

• Fujinami Shuhei

• Ukaji Yutaka

• Inomata Katsuhiko

• 藤波 修平

• 宇梶 裕

• 猪股 勝彦

抄録

金沢大学理工研究域物質化学系

The asymmetric addition of alkynylzinc reagents, prepared in situ from dimethylzinc and 1-alkynes, to α-dinitrones derived from glyoxal and N-(4-isopropylbenzyl)hydroxylamine was investigated by utilizing dicyclohexyl (R,R)-tartrate as a chiral auxiliary. The addition reaction of methyl(2-phenylethynyl)zinc afforded the corresponding optically active C2-symmetric (R,R)-bis(hydroxylamine) derivative with enantioselectivities of 90% and 81% ee by utilizing a stoichiometric and catalytic amount of the tartrate, respectively. Furthermore, the catalytic addition reaction of several alkynylzinc reagents also furnished the corresponding bis(hydroxylamine) with moderate to good enantioselectivities. © 2008 Elsevier Ltd. All rights reserved.

収録刊行物

• Tetrahedron Asymmetry

  Tetrahedron Asymmetry 19 (8), 921-931, 2008-05-01

  Elsevier

詳細情報

• CRID: 1390857226428642432
• NII論文ID: 120001135615
• NII書誌ID: AA1074621X
• ISSN: 09574166
• DOI: 10.24517/00010230
• Web Site: http://hdl.handle.net/2297/9878
• 本文言語コード: en
• データソース種別:
  • JaLC
  • IRDB
  • CiNii Articles