Desymmetrization of 1,4-Pentadien-3-ol by the Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imines

作者：Yoshida Mari; Sassa Naotaro; Kato Tomomitsu; Fujinami Shuhei; Soeta Takahiro; Inomata Katsuhiko; Ukaji Yutaka^*

来源：Chemistry - A European Journal, 2014, 20(7): 2058-2064.

DOI：10.1002/chem.201302889

• azomethine imines
• cycloaddition
• desymmetrization
• diisopropyl tartrate
• pyrazolidines

Desymmetrization of the divinyl carbinol 1,4-pentadien- 3-ol was accomplished by the asymmetric 1,3-dipolar cycloaddition of azomethine imines based on a magnesium-mediated, multinucleating chiral reaction system utilizing diisopropyl (R, R)-tartrate as the chiral auxiliary. The corresponding optically active trans-pyrazolidines, each with three contiguous stereogenic centers, were obtained with excellent regio-, diastereo-, and enantioselectivity, with results as high as 99% ee. This reaction was shown to be applicable to both aryl-and alkyl-substituted azomethine imines. The use of a catalytic amount of diisopropyl (R, R)-tartrate was also effective when accompanied by the addition of MgBr2.

• 出版日期2014-2-10