Evaluation of (+)-sparteine-like diamines for asymmetric synthesis |
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Authors: | Dearden Michael J McGrath Matthew J O'Brien Peter |
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Institution: | Department of Chemistry, University of York, Heslington, York YO10 5DD, United Kingdom. |
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Abstract: | Three new (+)-sparteine-like diamines were prepared from (-)-cytisine and evaluated as sparteine surrogates in the alpha-lithiation rearrangement of cyclooctene oxide and the palladium(II)/diamine catalyzed oxidative kinetic resolution of 1-indanol. The new diamines exhibited opposite enantioselectivity to that observed with (-)-sparteine but increasing the steric hindrance of the N-alkyl group beyond N-Et had a detrimental effect on enantioselectivity. The optimal N-Me diamine was evaluated with much success in five other (-)-sparteine-mediated processes involving different metals (lithium, magnesium, and copper) and different types of reaction mechanisms. |
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