Desymmetrization of 1,4‐Pentadien‐3‐ol by the Asymmetric 1,3‐Dipolar Cycloaddition of Azomethine Imines
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<jats:title>Abstract</jats:title><jats:p>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 (<jats:italic>R</jats:italic>,<jats:italic>R</jats:italic>)‐tartrate as the chiral auxiliary. The corresponding optically active <jats:italic>trans</jats:italic>‐pyrazolidines, each with three contiguous stereogenic centers, were obtained with excellent regio‐, diastereo‐, and enantioselectivity, with results as high as 99 % <jats:italic>ee</jats:italic>. This reaction was shown to be applicable to both aryl‐ and alkyl‐substituted azomethine imines. The use of a catalytic amount of diisopropyl (<jats:italic>R</jats:italic>,<jats:italic>R</jats:italic>)‐tartrate was also effective when accompanied by the addition of MgBr<jats:sub>2</jats:sub>.</jats:p>
収録刊行物
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- Chemistry – A European Journal
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Chemistry – A European Journal 20 (7), 2058-2064, 2014-01-08
Wiley
