Tuning the Chiral Environment of C2-Symmetric Diene Ligands: Development of 3,7-Disubstituted Bicyclo[3.3.1]nona-2,6-dienes
- 2 December 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 74 (2), 869-873
- https://doi.org/10.1021/jo802437h
Abstract
Through the structural analysis of bicyclo[3.3.1]nona-2,6-dienes, new C(2)-symmetric chiral diene ligands 1 based on 3,7-disubstituted bicyclo[3.3.1]nona-2,6-diene framework have been designed and synthesized. These chiral ligands readily bind to rhodium(I) and provide a different chiral environment from the existing chiral dienes. The rhodium complexes thus obtained act as effective catalysts for 1,4-addition of alkenyl- and arylboronic acids to various alpha,beta-unsaturated ketones, including several combinations that were previously difficult to provide high enantioselectivity.Keywords
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