Expedient, high-yielding synthesis of silyl-substituted salen ligands |
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Authors: | Thadani Avinash N Huang Yong Rawal Viresh H |
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Affiliation: | Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA. |
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Abstract: | Described is an efficient synthesis of silyl-substituted salen ligands, used for the preparation of enantioselective catalysts. The salicylaldehyde precursors are synthesized from the silyl ethers of 2,6-dibromophenols via a one-pot double lithium halogen exchanges, to induce an intramolecular retro-Brook rearrangement and allow introduction of the aldehyde group. Condensation of the salicylaldehyde products with a chiral diamine affords the silyl-substituted salen ligands in high yields. The use of other electrophiles allows easy access to silyl-substituted phenolic esters, ketones, and boronic acids. |
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