A new class of nitrogen based chiral ligands: 2H-1,3-benzoxazines. Ligand synthesis, X-ray structural studies and asymmetric catalysis |
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| Authors: | Neeranat Thienthong Patrick Perlmutter |
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| Institution: | Centre for Green Chemistry, School of Chemistry, Monash University, P.O. Box 23, Clayton, Melbourne 3800, Australia |
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| Abstract: | A new class of chiral ligands, e.g., (−)-9, based on the benzoxazine nucleus, has been designed and synthesized in three steps from the commercially available starting materials salicylamide and (−)-menthone. Application of (−)-9 in the palladium catalyzed-allylic substitution of 1,3-diphenyl-2-propenylacetate with dimethyl malonate gave enantioselectivities of up to 62%ee. Ees of 42% and 20% in asymmetric hydrosilylations and diethylzinc additions, respectively, were also obtained. |
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| Keywords: | 2H-1 3-benzoxazines Ligand Crystal structures Enantioselective Allylation Diethylzinc addition Hydrosilylation |
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