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Synfacts 2005(0): 0056-0056
DOI: 10.1055/s-2005-869942
DOI: 10.1055/s-2005-869942
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Enantioselective Diethylzinc Addition to Alde-hydes Catalyzed by Dialkylaminoisoborneols
Y. Hari, T. Aoyama*
Nagoya City Universoty, Japan
Further Information
Publication History
Publication Date:
20 July 2005 (online)
Significance
A novel ligand based on the (1R,2R)-10-dialkylaminoisoborneol structure possessing a 9-azabicyclo[3.3.1]nonan-9-yl group has efficiently catalyzed the enantioselective addition of diethylzinc to aldehydes. The ligand can be easily prepared in three steps from camphorsulfonyl chloride. Eight other ligands based on the dialkylaminoisoborneol structure were also evaluated, but the bulky 9-azabicyclo[3.3.1]nonan-9-yl group gave the highest enantioselectivity and yield. The application of alkylzinc addition to aromatic, aliphatic and vinylic aldehydes was reported.